DC Citi Open round of 16 picks and predictions: Bets bets on Ben Shelton vs. Gabriel Diallo and Emma Raducanu vs. Naomi Osaka

DC Citi Open predictions

The DC Citi Open Round of 16 continues on Thursday, and I’ve got two picks for the action.

The pregame narrative: Canadian Gabriel Diallo is a slight underdog against ATP No. 9-ranked Ben Shelton. Both are strong servers, and their matchup should go down to the wire. On the women’s side, Naomi Osaka meets Emma Raducanu in a battle of two Grand Slam winners.

Check out my top DC Citi Open predictions for July 24.

DC Citi Open predictions overview

Tennis predictionsOdds
Shelton/Diallo over 24.5 games-106
Osaka to win-125

Go to full DC Citi Open betting markets

DC Citi Open predictions made at 4:00 p.m. ET on 07/23/25.

DC Citi Open predictions

Best Bet: Shelton/Diallo over 23.5 games (-106)

If you’re a fan of long rallies, this match probably isn’t for you.

Shelton and Diallo are two of the hardest-serving players on the ATP Tour, ranking 14th and 15th in aces per match. Both players rank inside the top-25 in service games won, and serve rating, too.

But as returners, they leave a lot to be desired. Diallo sits 57th in return games won (19.0%), and Shelton is even lower at 73 (15.4%).

With that said, I think breaks will come few and far between, and can easily see this going the distance with a couple of tiebreaks.

Shelton is the favourite, and deservingly so, but Diallo is playing the best tennis of his young career.

The Canadian won his first ATP singles event at the Libema Open in June and took ATP World No. 4 Taylor Fritz to a fifth set in a Wimbledon second-round thriller.

Key stat: Diallo won his only match against Shelton 5–7, 7–6, 6–3 in 2022.

Quick pick

Osaka to win (-125): It’s officially comeback season for Osaka.

The former WTA World No. 1 took a leave of absence in 2023 and was shaky in 2024. But she’s put together a strong 21-10 record this year and, as expected, is doing her best work on hard courts, where she won all four of her slams.

Osaka is 10-4 on the surface this year and 4-1 in her last five. It’s worth noting two of those losses came via retirements, and one was in the Auckland Open final when she held a one-set lead.

Raducanu’s lone Grand Slam also came on hard court (2021 US Open), but she has been an unimpressive 32-29 (52.4%) on the surface since then.

The Englishwoman is also playing doubles in this event, which should make things a little more difficult against Osaka, who is consistently pushing her competitors deep into matches.

Osaka has only lost in straight sets twice in 31 matches this season.

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Avery joined NorthStar Gaming as an intern in 2022 before stepping into a full-time role soon after. He loves betting on and analyzing golf — mainly because it’s easier than actually playing — but is a fan of all sports, from the NFL to the UFC.