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Red Sox vs. Diamondbacks SGP predictions Sept. 5: Back rookie pitcher Tolle, Boston at +450

The Boston Red Sox look to gain ground in the AL East race during their three-game set against the Arizona Diamondbacks beginning on Friday.

The pregame narrative: Boston is 3.5 games back of the Toronto Blue Jays, who are in New York for a pivotal series against the Yankees. The Red Sox, now without Roman Anthony, are a slight favourite with rookie Payton Tolle going opposite Eduardo Rodriguez.

Check out my Red Sox vs. Diamondbacks SGP predictions for Sept. 5, featuring Tolle and Rob Refsnyder.

Red Sox vs. Diamondbacks predictions

Parlay: Red Sox F5 +0.5 | Tolle over 4.5 Ks | Refsnyder 1+ RBI (+450)

Red Sox F5 +0.5 (-162): I want to tap into what I perceive to be a pitching advantage in Boston’s favour.

Tolle has only made one MLB start, and it was solid. He fanned eight Pittsburgh Pirates over 5.1 innings of two-run ball. I’ll circle back on the rookie later, but believe he’s due for another strong outing.

Rodriguez, meanwhile, has a massive MLB sample, and it’s ugly.

The southpaw owns a 5.40 ERA this season and has gotten routinely shelved at Chase Field, MLB’s third-most hitter-friendly environment, according to Baseball Savant’s Park Factors.

Boston’s active lineup has a successful history against Rodriguez over a large sample, too.

The Sox are a collective 22-for-67 against him with a .612 slugging percentage. I expect them to be at least tied through five frames.

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MLB SGP legs

Tolle over 4.5 Ks (-152): Back to the 6-foot-6, moustachioed 22-year-old southpaw.

Tolle was torching the minor leagues before joining the Sox. He had a 3.04 ERA with a blistering 13.1 K/9 rate in 18 starts this year.

The Texas Christian product has an upper-90s fastball/cutter combo and a 99th percentile “extension,” which essentially measures how far from the rubber he releases his pitches.

That makes his offerings appear even faster for opposing bats.

Arizona is a tough team to put away on strikes, especially for lefties, but Tolle has generated great swing-and-miss at every level and will have the advantage of seeing this lineup for the first time.

Refsnyder 1+ RBI (+170): Refsnyder only has 23 RBI on the season, but this is oozing with value.

He’s slated to hit fifth for Boston tonight, according to Rotowire, behind names like Alex Bregman and Trevor Story.

That duo has reached base safely in a combined 18-of-42 plate appearances against Rodriguez (.428 OBP). Refsnyder is just 2-for-10 against the lefty, but he has a .392 xBA in those at-bats, so I expect some positive regression.

And on the season, Refsnyder has demolished left-handed pitching to the tune of a .304/.395/.559 slash line.

This is a great price for a player in a run-producing spot.

Red Sox vs. Diamondbacks predictions made at 11:26 a.m. ET on 09/05/2025.

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Blue Jays vs. Yankees best bets Sept. 5: Bet on Judge, Springer to lead offence in series opener

The Toronto Blue Jays and New York Yankees begin a massive three-game series in the Bronx on Friday.

The pregame narrative: Toronto holds a three-game lead over New York in the AL East standings and is a slight road underdog tonight behind the red-hot Kevin Gausman. New York counters with rookie standout Cam Schlittler, who owns a 2.61 ERA across nine starts.

Check out my Blue Jays best bets vs. the Yankees for Sept. 3, featuring Aaron Judge and George Springer.

Blue Jays best bets vs. Yankees

Best bet: Judge over 1.5 bases (-112)

Judge is “slumping”, but I’ll happily take his bases total when it’s favourably priced in a solid matchup.

The Yankees’ slugger still leads MLB in batting average (.321), slugging percentage (.663), ISO (.341) and wRC+ (193) despite posting a .242/.415/.474 slash line since August 1.

That .415 on-base percentage is a reflection of Judge’s plate discipline and his opponents’ willingness to walk him in high-leverage situations.

He had more walks (27) than hits (23) in that span, which isn’t ideal for this wager.

Still, he’s gone over this line in five of his last 10 games — with three home runs — and has dominated Gausman in a large sample size.

Judge is 16-for-43 against Gausman with three doubles and six home runs.

In those PAs, his xBA (.382) and xSLG (.876) are better than his normal numbers (.356, .822).

Gausman is finding his form at the right time, with a 3.06 ERA and sub-1.00 WHIP in his last 10 starts. A lot of that success has been due to his elite command, though, meaning Judge should get something to swing at tonight.

Key stat: Judge leads MLB in total bases per game (2.41).

Jays prop picks

Springer to score (-154): You know who’s not slumping? George Springer.

Toronto’s leadoff man is on a rampage and should, in my opinion, earn down-ballot MVP votes with the way he’s closing out the season. Check out his MLB ranks post-all-star-game:

First in batting average (.405)
First in wRC+ (238)
Second in on-base percentage (.496)
Second in OPS (1.235)

Springer has reached base in nearly half of his 131 plate appearances since July 17, scoring a blistering 37 runs in 28 games.

Schlittler is a solid arm, no doubt, but I’ll back Springer at this price any day, and I trust Toronto’s lineup to drive him home.

Over 9 runs (+100): The Jays lead MLB in batting average (.294), OPS (.857) and wRC+ (137) in the second half. That’s why I’m not worried about them getting after Schlittler and scoring Springer.

Toronto scored 25 runs in its last two games against the Cincinnati Reds, and is 6-2-1 against this line in its last 10 games.

When the Jays faced Schlittler in July, they had seven hits and three walks in 5.0 IP but only managed two runs. That’s an anomaly.

These teams have played seven games dating back to Toronto’s four-game sweep of New York in June. Those outings averaged 12.14 runs, and the over on this total went 4-2-1.

Blue Jays best bets made at 9:03 a.m. ET on 09/05/2025.

Blue Jays vs. Yankees best bets Sept. 5: Bet on Judge, Springer to lead offence in series opener

The Toronto Blue Jays and New York Yankees begin a massive three-game series in the Bronx on Friday.

The pregame narrative: Toronto holds a three-game lead over New York in the AL East standings and is a slight road underdog tonight behind the red-hot Kevin Gausman. New York counters with rookie standout Cam Schlittler, who owns a 2.61 ERA across nine starts.

Check out my Blue Jays best bets vs. the Yankees for Sept. 3, featuring Aaron Judge and George Springer.

Blue Jays best bets vs. Yankees

Best bet: Judge over 1.5 bases (-103)

Judge is “slumping”, but I’ll happily take his bases total when it’s favourably priced in a solid matchup.

The Yankees’ slugger still leads MLB in batting average (.321), slugging percentage (.663), ISO (.341) and wRC+ (193) despite posting a .242/.415/.474 slash line since August 1.

That .415 on-base percentage is a reflection of Judge’s plate discipline and his opponents’ willingness to walk him in high-leverage situations.

He had more walks (27) than hits (23) in that span, which isn’t ideal for this wager.

Still, he’s gone over this line in five of his last 10 games — with three home runs — and has dominated Gausman in a large sample size.

Judge is 16-for-43 against Gausman with three doubles and six home runs.

In those PAs, his xBA (.382) and xSLG (.876) are better than his normal numbers (.356, .822).

Gausman is finding his form at the right time, with a 3.06 ERA and sub-1.00 WHIP in his last 10 starts. A lot of that success has been due to his elite command, though, meaning Judge should get something to swing at tonight.

Key stat: Judge leads MLB in total bases per game (2.41).

Embed: #117570

Jays prop picks

Springer to score (-121): You know who’s not slumping? George Springer.

Toronto’s leadoff man is on a rampage and should, in my opinion, earn down-ballot MVP votes with the way he’s closing out the season. Check out his MLB ranks post-all-star-game:

First in batting average (.405)
First in wRC+ (238)
Second in on-base percentage (.496)
Second in OPS (1.235)

Springer has reached base in nearly half of his 131 plate appearances since July 17, scoring a blistering 37 runs in 28 games.

Schlittler is a solid arm, no doubt, but I’ll back Springer at this price any day, and I trust Toronto’s lineup to drive him home.

Over 9 runs (+100): The Jays lead MLB in batting average (.294), OPS (.857) and wRC+ (137) in the second half. That’s why I’m not worried about them getting after Schlittler and scoring Springer.

Toronto scored 25 runs in its last two games against the Cincinnati Reds, and is 6-2-1 against this line in its last 10 games.

When the Jays faced Schlittler in July, they had seven hits and three walks in 5.0 IP but only managed two runs. That’s an anomaly.

These teams have played seven games dating back to Toronto’s four-game sweep of New York in June. Those outings averaged 12.14 runs, and the over on this total went 4-2-1.

Blue Jays best bets made at 9:03 a.m. ET on 09/05/2025.

Jannik Sinner vs. Felix Auger-Aliassime US Open semifinal odds and best bet: Canadian faces uphill battle as massive underdog on Friday

Jannik Sinner and Felix Auger-Aliassime battle for a spot in the U.S. Open final on Friday.

The pre-match narrative: This figures to be a lopsided affair. Sinner, the World No. 1 and reigning champion, has only dropped one set at Flushing Meadows and is -2,500 to advance. Auger-Aliassime has had a resurgent year but was beaten handily the last time he played Sinner.

Check out our Sinner vs. Auger-Aliassime odds and my best bet for the Sept. 5 tennis match.

Sinner vs. Auger-Aliassime odds

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Full U.S. Open betting markets

Best US Open men’s tennis pick

Best Bets: Auger-Aliassime over 0.5 breaks (-148)

There isn’t much value in betting on this match.

Sinner is -200 to win this match in straight sets, and has a lofty -7.5 game spread, which could admittedly go either way.

The Italian has only been broken three times at Flushing Meadows, all at the hands of Auger-Aliassime’s fellow Canadian, Denis Shapovalov.

Sinner still won that match 5-7, 6-4, 6-3, 6-3, and has since demolished Alexander Bublik and Lorenzo Musetti, dropping a total of 10 games across six sets.

I can’t picture a world where Auger-Aliassime gives Sinner trouble. But a single break? That’s attainable.

The Montreal native has knocked off two top-10 players in this event, Alex de Minaur and Alexander Zverev, generating 15 break opportunities in those matches.

He also breezed past 15-seed Andrey Rublev, converting 4-of-7 breaks in that match.

Auger-Aliassime is 2-1 against Sinner in his career, but was most recently dismantled, 6-0, 6-2, by the Italian in Cincinnati. But even then, the Canadian cashed this wager.

Key stat: Auger-Aliassime has converted 8-of-16 career break points against Sinner.

Sinner vs. Auger-Aliassime best bet made at 2:30 p.m. on 09/04/2025.

Best NFL Week 1 prop bets: Back David Montgomery, Marvin Harrison Jr. on Sunday

Two wide receivers and one running back make up this week’s NFL prop picks.

The pregame narrative: Marvin Harrison Jr. underwhelmed last year, but gets a fantastic matchup to set the tone in his sophomore campaign. Elsewhere, David Montgomery’s modest rushing total against the Green Bay Packers has caught my attention.

Check out my top Week 1 NFL prop bets, featuring a prediction on Cleveland Browns wideout Cedric Tillman.

NFL prop bets: Week 1

Best bet: Tillman over 40.5 receiving yards (-113)

This is far from flashy, but Tillman has an opportunity to make a name for himself this season.

Slotting in as Cleveland’s WR2, he’ll be getting plenty of looks from 40-year-old gunslinger Joe Flacco.

Flacco averaged an incredible 251.6 passing yards across seven starts with the Indianapolis Colts last year, while throwing the ball 35 times a game.

Cleveland will likely be down big against the Cincinnati Bengals’ electric offence, and that should force first-year offensive coordinator Tommy Rees into a pass-heavy game plan right off the bat.

Enter Tillman, who was finding solid form in 2024 before suffering a concussion. The then-sophomore averaged 66 receiving yards across his last five games, clearing this line four times.

Cincinnati’s biggest problem last year was its defence. The group gave up 7.6 yards per attempt on third downs last year, which ranked 27th, and made no changes except letting one of its best corners, Mike Hilton, walk into free agency.

This has all the makings of a smash play.

Key stat: Tillman caught eight of 12 passes for 81 yards in his lone start against the Bengals last year.

Best NFL picks

Montgomery over 41.5 rushing yards (-118): This should be the year where Jahmyr Gibbs breaks out of his timeshare with Montgomery, but I still expect a heavy dose of the veteran tailback in Sunday’s season-opener.

Before his injury in Week 15 against the Buffalo Bills, Montgomery was averaging 59.3 rushing yards at a healthy 4.28 yards per carry.

He was 7-6 against this line, clearing it in both games against the Packers.

The acquisition of Micah Parsons unquestionably makes Green Bay’s defence better as a whole, but sending three-time Pro-Bowl defensive tackle Kenny Clark the other way leaves a gap on the defensive line.

Dan Campbell will want to exploit that early, and that means Montgomery and Gibbs will have their fair share of attempts.

Harrison over 58.5 receiving yards (-118): Harrison hauled in 62 catches for 885 yards and eight touchdowns as a rookie last year.

Most players would kill for numbers like that, but it didn’t quite live up to the hype a No. 4 overall pick demands. The good news is there is plenty of room to grow.

Harrison had 116 targets last year, which ranked 29th in the NFL.

His 1,566 targeted air yards ranked sixth among all receivers, per Player Profiler.

He was targeted on 46.4% of Arizona’s deep balls, which ranked seventh among receivers.

Kyler Murray said there was a “night and day” difference regarding his chemistry with Harrison from when he was drafted until now. That’s probably just QB speak, but I’ll buy in on the hype train — in this matchup, at least.

Harrison and Co. go up against a New Orleans Saints team which lost two starting corners, four-time Pro Bowler Marshon Lattimore and Paulson Adebo.

NFL prop bets made at 10:30 a.m. ET on 09/04/2025.

Best NFL Week 1 prop bets: Back David Montgomery, Marvin Harrison Jr. on Sunday

Two wide receivers and one running back make up this week’s NFL prop picks.

The pregame narrative: Marvin Harrison Jr. underwhelmed last year, but gets a fantastic matchup to set the tone in his sophomore campaign. Elsewhere, David Montgomery‘s modest rushing total against the Green Bay Packers has caught my attention.

Check out my top Week 1 NFL prop bets, featuring a prediction on Cleveland Browns wideout Cedric Tillman.

NFL prop bets: Week 1

Best bet: Tillman over 38.5 receiving yards (-113)

This is far from flashy, but Tillman has an opportunity to make a name for himself this season.

Slotting in as Cleveland’s WR2, he’ll be getting plenty of looks from 40-year-old gunslinger Joe Flacco.

Flacco averaged an incredible 251.6 passing yards across seven starts with the Indianapolis Colts last year, while throwing the ball 35 times a game.

Cleveland will likely be down big against the Cincinnati Bengals’ electric offence, and that should force first-year offensive coordinator Tommy Rees into a pass-heavy game plan right off the bat.

Enter Tillman, who was finding solid form in 2024 before suffering a concussion. The then-sophomore averaged 66 receiving yards across his last five games, clearing this line four times.

Cincinnati’s biggest problem last year was its defence. The group gave up 7.6 yards per attempt on third downs last year, which ranked 27th, and made no changes except letting one of its best corners, Mike Hilton, walk into free agency.

This has all the makings of a smash play.

Key stat: Tillman caught eight of 12 passes for 81 yards in his lone start against the Bengals last year.

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Best NFL picks

Montgomery over 42.5 rushing yards (-114): This should be the year where Jahmyr Gibbs breaks out of his timeshare with Montgomery, but I still expect a heavy dose of the veteran tailback in Sunday’s season-opener.

Before his injury in Week 15 against the Buffalo Bills, Montgomery was averaging 59.3 rushing yards at a healthy 4.28 yards per carry.

He was 7-6 against this line, clearing it in both games against the Packers.

The acquisition of Micah Parsons unquestionably makes Green Bay’s defence better as a whole, but sending three-time Pro-Bowl defensive tackle Kenny Clark the other way leaves a gap on the defensive line.

Dan Campbell will want to exploit that early, and that means Montgomery and Gibbs will have their fair share of attempts.

Harrison over 55.5 receiving yards (-115): Harrison hauled in 62 catches for 885 yards and eight touchdowns as a rookie last year.

Most players would kill for numbers like that, but it didn’t quite live up to the hype a No. 4 overall pick demands. The good news is there is plenty of room to grow.

Harrison had 116 targets last year, which ranked 29th in the NFL.

His 1,566 targeted air yards ranked sixth among all receivers, per Player Profiler.

He was targeted on 46.4% of Arizona’s deep balls, which ranked seventh among receivers.

Kyler Murray said there was a “night and day” difference regarding his chemistry with Harrison from when he was drafted until now. That’s probably just QB speak, but I’ll buy in on the hype train — in this matchup, at least.

Harrison and Co. go up against a New Orleans Saints team which lost two starting corners, four-time Pro Bowler Marshon Lattimore and Paulson Adebo.

NFL prop bets made at 10:30 a.m. ET on 09/04/2025.

Chiefs vs. Chargers Week 1 picks: Prop predictions on Isiah Pacheco, Keenan Allen for Friday’s game in Brazil

The Kansas City Chiefs and Los Angeles Chargers open their seasons with a Friday night showdown in Sao Paulo, Brazil.

The pregame narrative: Kansas City fell short of a historic three-peat last season but is still loaded with talent on both sides of the ball. The Chiefs are modest 3-point favourites as of Monday afternoon against a Chargers team looking to build on Jim Harbaugh’s successful maiden coaching campaign.

Check out my Chiefs vs. Chargers picks for the game on Sept. 5, featuring prop bets on Isiah Pacheco and Keenan Allen.

Chiefs vs. Chargers picks

Best bet: Pacheco over 60.5 rushing and receiving yards (-118)

I’m of the mind that we can throw Pacheco’s 2024 season out of the window.

The running back suffered a fractured fibula in Week 2 and never regained his starting role after that, slipping into a timeshare with veteran Kareem Hunt upon his return in Week 13. But take a look at what he did in the two weeks before the injury:

Week 1 vs. BAL: 45 rushing yards, 33 receiving yards
Week 2 vs. CIN: 90 rushing yards, 21 receiving yards

And the year before that? Pacheco averaged 66.8 rushing yards and 17.4 receiving yards per game as a sophomore.

He went 9-5 against this line and had a healthy 60% snap share.

Assuming Pacheco is fully healthy for this season, and all reports indicate he is, this line should be a laugher. I don’t care how good Los Angeles’ defence is; Pacheco is a bell-cow back who can catch and should be fed early and often.

Also, Pacheco logged 61 scrimmage yards with a 46% snap share in his Week 14 matchup with the Chargers last season.

Key stat: Pacheco was 16-4 against this line from the start of the 2023 season up until his injury in Week 2 last year (playoffs included).

NFL Brazil game prop pick

Allen over 3.5 receptions (-138): You might be reading this thinking: “Wait, since when is Allen back on the Chargers?”

I wouldn’t blame you for that one, as the veteran joined camp less than a month ago on a one-year “prove-it” deal.

But I don’t think the 33-year-old is washed, and I believe he’ll slide in as a solid No. 2 behind sophomore Ladd McConkey, especially with Quentin Johnston (concussion) possibly sidelined.

Allen earned 121 targets in a deep Chicago Bears receiving room last year, is sure-handed (he only had six drops all year), and can still create a good amount of separation at the line.

His familiarity with Herbert will certainly be a boost, too.

Allen had three-plus receptions in 14 of 15 games last year, going 10-5 against this line.

Chiefs vs. Chargers picks made at 10:43 a.m. ET 09/01/2025.

Yankees vs. Astros SGP predictions Sept. 4: Bet on Houston, Yordan Alvarez in series finale

The New York Yankees and Houston Astros play out their rubber match at Daikin Park on Thursday night.

The pregame narrative: New York is a slight favourite with Carlos Rodon on the mound, who is pitching opposite Houston’s Cristian Javier. The Astros righty is making his fifth start of the season and has dominated the Yankees in the past.

See why I like plenty of offence in my Yankees vs. Astros SGP predictions for Sept. 4, featuring Yordan Alvarez.

Yankees vs. Astros predictions

Parlay: Astros +2.5 | Alvarez over 1.5 bases | Rodon over 3.5 Ks (+270)

Astros +2.5 (-250): This seems like a no-brainer way to begin the SGP.

Javier doesn’t have a massive body of work this season, but owns a respectable 3.38 ERA across four starts.

Most recently, he threw six no-hit innings against the Los Angeles Angels on Aug. 29.

The righty has some command issues, to be fair, but so does Rodon, who walked a shocking 20 batters in 34.1 innings in August.

And take a look at how each pitcher has performed against their opposing lineup:

Yankees vs. Javier: 11-for-61 (.180 BA, .195 xBA), 34.8% K rate
Astros vs. Rodon: 28-for-103 (.272 BA, .241 XBA), 26.1% K rate

Rodon’s road ERA (3.47) and OBA (.225) are also notably higher than his numbers at home (2.86 ERA, .145 OBA).

I feel comfortable banking two runs with the 77-win Astros.

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MLB SGP legs

Alvarez over 1.5 bases (+120): The biggest risk with this leg, in my opinion, is Alvarez taking walks.

Rodon is issuing free passes like cutout coupons, and Alvarez has had an 80th percentile or higher walk rate in each of the last four seasons.

But getting one of baseball’s most dangerous hitters at plus money seems too good to pass up on.

Alvaraez is batting .318 with a .545 SLG in 22 at-bats vs. LHP this season, and ran even better reverse splits in last year’s full-season sample:

2024 vs. LHP: .362/.411/.617
2024 vs. RHP: .280/.383/.541

The slugger is 6-for-9 in this series with a double and should stay hot.

Rodon over 3.5 Ks (-500): Betting a -500 prop as a standalone never plays, but this leg brings this wager from +175 to +270, which is well worth it.

Rodon’s 26.5% K rate ranks in the 78th percentile. He’s gone over this line in 26-of-28 starts and has cleared this mark in all four starts vs. Houston since joining New York.

There isn’t much more to say here. This is an extremely manageable line for a solid pitcher.

Yankees vs. Astros predictions made at 9:23 a.m. ET on 09/04/2025.

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Novak Djokovic vs. Carlos Alcaraz US Open semifinal odds and best bet: Take the over in star-studded matchup

Novak Djokovic and Carlos Alcaraz meet in a must-see U.S. Open semifinal match this Friday.

The pre-match narrative: When these two battle, the stakes are often high. Djokovic is 5-3 against Alcaraz with a perfect 3-0 record on hard courts. The 24-time Grand Slam champion has won their last two meetings but is an underdog against Alcaraz, who has yet to drop a set at Flushing Meadows.

Check out our Djokovic vs. Alcaraz odds and my best bet for the Sept. 5 tennis match.

Djokovic vs. Alcaraz odds

Market	Odds
Djokovic to win	+275
Alcaraz to win	-400
Djokovic +5.5 games	-120
Alcaraz -5.5 games	-112
Djokovic +1.5 sets	+130
Alcaraz -1.5 sets	-182
Over 3.5 sets	-154
Under 3.5 sets	+115
Over 37.5 games	-118
Under 37.5 games	-118

Full U.S. Open betting markets

Best US Open men’s tennis pick

Best Bets: Over 3.5 sets (-154)

Is this a lot of juice? Yes, but I think it’s worth the squeeze in this semifinal.

I was skeptical about Djokovic’s conditioning coming into this tournament, but it’s clear Father Time will have to wait before calling the Serbian’s number.

Djokovic has improved round over round and just beat the last remaining American, No. 4-ranked Taylor Fritz (6-3, 7-5, 3-6, 6-4).

Nerves were clearly affecting Fritz, who only hit 59% of his first serves while converting just two of 13 break-point chances (15.4%).

No one should expect Alcaraz to play like that, but I’m still bullish on Djokovic pushing this to at least four sets and perhaps five.

Another wager I’m making is Djokovic +1.5 sets at +130.

Djokovic is 4-1 in his last five matches against Alcaraz. That includes a win at this year’s Australian Open and a straight-sets victory at the 2023 Nitto ATP Finals.

Both players will have two days’ rest between their quarterfinal matchups on Tuesday and Friday’s semifinal showdown. That should favour the 38-year-old underdog.

Alcaraz has dropped at least one set in eight of his last nine Grand Slam matches against top-10 players, including each of his last five.

Key stat: Alcaraz has only beaten Djokovic in straight sets once (2024 Wimbledon final) in their eight meetings.

Djokovic vs. Alcaraz best bet made at 12 p.m. on 09/03/2025.

Novak Djokovic vs. Carlos Alcaraz US Open semifinal odds and best bet: Take the over in star-studded matchup

Novak Djokovic and Carlos Alcaraz meet in a must-see U.S. Open semifinal match this Friday.

The pre-match narrative: When these two battle, the stakes are often high. Djokovic is 5-3 against Alcaraz with a perfect 3-0 record on hard courts. The 24-time Grand Slam champion has won their last two meetings but is an underdog against Alcaraz, who has yet to drop a set at Flushing Meadows.

Check out our Djokovic vs. Alcaraz odds and my best bet for the Sept. 5 tennis match.

Djokovic vs. Alcaraz odds

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Full U.S. Open betting markets

Best US Open men’s tennis pick

Best Bets: Over 3.5 sets (-150)

Is this a lot of juice? Yes, but I think it’s worth the squeeze in this semifinal.

I was skeptical about Djokovic’s conditioning coming into this tournament, but it’s clear Father Time will have to wait before calling the Serbian’s number.

Djokovic has improved round over round and just beat the last remaining American, No. 4-ranked Taylor Fritz (6-3, 7-5, 3-6, 6-4).

Nerves were clearly affecting Fritz, who only hit 59% of his first serves while converting just two of 13 break-point chances (15.4%).

No one should expect Alcaraz to play like that, but I’m still bullish on Djokovic pushing this to at least four sets and perhaps five.

Another wager I’m making is Djokovic +1.5 sets at +148.

Djokovic is 4-1 in his last five matches against Alcaraz. That includes a win at this year’s Australian Open and a straight-sets victory at the 2023 Nitto ATP Finals.

Both players will have two days’ rest between their quarterfinal matchups on Tuesday and Friday’s semifinal showdown. That should favour the 38-year-old underdog.

Alcaraz has dropped at least one set in eight of his last nine Grand Slam matches against top-10 players, including each of his last five.

Key stat: Alcaraz has only beaten Djokovic in straight sets once (2024 Wimbledon final) in their eight meetings.

Djokovic vs. Alcaraz best bet made at 12 p.m. on 09/03/2025.