The WTA Finals Riyadh continue Monday with the Serena Williams (singles) and Martina Navratilova (doubles) groups back in action for their second round-robin matches.
Iga Swiatek and Elena Rybakina, both coming off dominant wins in their openers, meet for the fifth time in 2025, while an arguably must-win American showdown is scheduled between Amanda Anisimova and Madison Keys, their inaugural meeting.
In doubles, the two victors from Saturday — Sara Errani-Jasmine Paolini and Hsieh Su-wei-Jelena Ostapenko — square off. Meanwhile, Veronika Kudermetova and Elise Mertens close play Monday against Demi Schuurs and Asia Muhammad.
Below is the order of play, advancement scenarios, match times and breakdowns of the four matches scheduled for Monday.
Serena Williams Group advancement scenarios
If Swiatek and Keys win:
• Swiatek advances as group winner
• Anisimova is eliminated
• Rybakina and Keys play for No. 2 spot Wednesday
If Swiatek wins in straight sets and Anisimova wins in three sets:
• Swiatek advances (position TBD)
• Keys is eliminated
WTA
If Rybakina and Anisimova win:
•Rybakina advances as group winner
•Keys is eliminated
•Swiatek and Anisimova play for No. 2 spot Wednesday
If Rybakina wins in straight sets and Keys wins in three sets:
•Rybakina advances (position TBD)
•Anisimova is eliminated
If there’s any other combination of results, advancement will be determined on final matches Wednesday.
Day 3 matchups
Note: All matches are local time.
Sara Errani and Jasmine Paolini (1) vs. Hsieh Su-wei and Jelena Ostapenko (6) — 3 p.m.
In their lone match this season, Errani and Paolini cruised past Hsieh and Ostapenko 6-4, 6-0 in the semifinals at the China Open last month. The Italians eventually won the title in Beijing — their third WTA 1000 doubles title of the season – and were the first pair to defend the doubles title at the event.
Ostapenko did defeat Paolini and Errani in the second round in Montreal this summer but competed alongside Barbora Krejcikova. A win would have either side in prime position to advance out of the group stage, a feat Errani and Paolini could not achieve in 2024.
Iga Swiatek (2) vs. Elena Rybakina (6) — Not before 5 p.m.
Head-to-Head: Swiatek leads 6-4
The Case for Swiatek: The head-to-head record doesn’t tell you that Swiatek dominated this series in 2025. The Polish national won all four matchups against Rybakina — Cincinnati, Roland Garros, Doha and the United Cup – and three were on hard court.
The Wimbledon singles champion looked dominant in her 61-minute 6-1, 6-2 win over Keys Saturday. Sure, Keys appeared rusty, but Swiatek ran Keys back-and-forth, won 82% of first service points and recorded just 12 unforced errors to Keys’ 33.
Interestingly, Swiatek can be become the first player to defeat the same opponent five times in the same year since… Swiatek herself did it in 2022 (Daria Katsakina).
The Case for Rybakina: Make no mistake, Rybakina has the toolkit to defeat Swiatek — the serve, the aggression and the consistency. Across those four losses to the World No. 2, the Kazakh won 39 games, and she still has four previous victories over Swiatek to her name.
Rybakina overpowered Anisimova Saturday in their first meeting, needing 57 minutes to notch a 6-3, 6-1 win. This season’s top server (475 aces) has lost only three games on her serve in her past six matches and saved 13 of 16 break points in that span. Can her powerful serve and experience break the streak against Swiatek?
Amanda Anisimova (4) vs. Madison Keys (7) — Not before 6:30 p.m.
Head-to-Head: Never played
The Case for Anisimova: Once again, Anisimova faces another opponent she’s yet to see in her career. Now, Saturday’s match against Rybakina was one to forget, but Anisimova’s no stranger to bouncing back and displaying her resiliency.
After an early exit at the Australian Open, Anisimova responded with a 1000-level title in Doha. Anisimova avenged her double-bagel loss to Swiatek in the Wimbledon singles final by defeating her in the quarterfinals at the US Open. She also just won a title in Beijing in her first tournament since losing to Aryna Sabalenka in the US Open final.
In 2025, Anisimova is 8-1 in matches following a loss played on hard court, and a win over Keys would also make Wednesday’s trilogy vs. Swiatek all the more interesting.
The case for Keys: It didn’t help that Keys’ first opponent in a 68-day break was Swiatek, and it wasn’t the version of Keys that won the Australian Open.
Maybe a brand-new opponent across the net will help Keys turn the page? When playing at her best, Keys’ forehand is a force to be reckoned with, but she’ll need to clean up the unforced errors. Over her break, Keys said she modified her serve and focused on coming to the net more, but couldn’t display the tactic much against Swiatek. Against Anisimova, who boasts a powerful return game, Keys must capitalize on her first serve, a key factor into her Australian Open title run.
Veronika Kudermetova and Elise Mertens (4) vs. Asia Muhammad and Demi Schuurs (8)
A win will go a long way if either side sees themselves advancing, with each dropping their respective matches Saturday.
Kudermetova and Mertens, after taking the first set 6-1, seemed in full control vs. Hsieh and Ostapenko, but their 4-2 lead in the second dwindled, and they fell in the 10-point match tie break. Schuurs and Muhammad lost in straight sets to Errani and Paolini, dropping the final four games of the second after having a 3-2 lead.
It’s been nearly half a year since these two teams squared off in the quarterfinals of the Internazionali BNL d’Italia. Kudermetova and Mertens won 3-6, 6-2 [10-4], eventually progressing to the final.
