Best Tennis Bets and Predictions for Thursday, August 20

The Cincinnati Open quarterfinals take center stage Thursday with four singles matches scheduled on P&G Center Court.

Amanda Anisimova vs. Jessica Pegula gets the singles card underway at 1 p.m. ET, followed by Tommy Paul vs. Flavio Cobolli, Iga Swiatek vs. Elena Rybakina, and Thiago Agustín Tirante vs. Arthur Fils.

We have our first bet locked in, with more plays coming as additional odds and markets become available.

We’re coming off a rough Wednesday, and you are invited to visit our Matchday Picks and Transparency Page for the most current results.

Thursday’s Cincinnati Open quarterfinal schedule

1:00 p.m. ET: Amanda Anisimova vs. Jessica Pegula
3:00 p.m. ET: Tommy Paul vs. Flavio Cobolli
7:00 p.m. ET: Iga Swiatek vs. Elena Rybakina
8:30 p.m. ET: Thiago Agustín Tirante vs. Arthur Fils

Amanda Anisimova vs. Jessica Pegula prediction

Best Bet: Over 20.5 games (-120 at Polymarket)

Jessica Pegula has won all five career meetings against Amanda Anisimova, including two hard-court victories in 2026, but this matchup has consistently produced enough resistance to push totals higher.

Four of their five meetings have reached at least 21 games, including all four since 2024. Anisimova has enough power to steal a set or extend one, while Pegula’s steadiness makes a complete collapse highly unlikely.

Rather than lay -207 with Pegula, we’ll take the better value on Over 20.5 games at –120 at Polymarket.

Tommy Paul vs. Flavio Cobolli prediction

Best Bet: Tommy Paul ML (-156 at Polymarket)

Tommy Paul gets our backing against Flavio Cobolli despite losing their only previous meeting here in Cincinnati.

Paul owns the much stronger recent statistical profile, posting a 1.338 Dominance Ratio compared to Cobolli’s 0.858 and a 1.545 Breakpoints Prevail Ratio to Cobolli’s 0.892.

Paul is also 20-10 on hard courts over the last 52 weeks and has won three straight matches.

We make Paul closer to a -185 favorite, giving us enough value to play the -156 moneyline at Polymarket.

Elena Rybakina vs. Iga Swiatek prediction

Best Bet: Elena Rybakina ML (+144 at Polymarket)

Iga Swiatek routed Elena Rybakina 6-2, 6-3 in Toronto earlier this month, but we are coming back on Rybakina in Cincinnati.

Rybakina owns a 46-9 hard-court record over the last 52 weeks and is 16-5 against Top-10 opponents during that span.

Rybakina also holds slight advantages in Dominance Ratio, Breakpoints Prevail, and Dominance Efficiency.

Swiatek leads the career series 7-6, but this matchup remains extremely close. We make tonight’s match essentially a coin flip and prefer Rybakina on the moneyline.

Phil Naessens

Phil Naessens has spent decades in sports as a broadcaster, author, journalist, professional tennis coach, and betting analyst. As the founder and editor of Crush & Rush News and host of the Crush & Rush Tennis Podcast, he combines firsthand coaching experience with years of sports media and publishing to deliver thoughtful tennis analysis, tournament coverage, player features, and transparent betting insights built around value, and not hype.