Swiatek and Anisimova set for winner-take-all showdown

The final round-robin matches are when things start to get juicier, and Day 5 of the WTA Finals Riyadh brings us a pair of winner-take-all matches.

In singles, a trilogy between Iga Swiatek and Amanda Anisimova will determine who takes second place in the Serena Williams Group. Elena Rybakina, who reigns as the guaranteed group winner, has a matchup against an already eliminated Madison Keys.

From the Martina Navratilova Group, top-seeded Sara Errani and Jasmine Paolini battle Veronika Kudermetova and Elise Mertens in their fourth meeting of 2025. The victor will take take second place and advance to the semifinals with Hsieh Su-wei and Jelena Ostapenko, who encounter Asia Muhammad and Demi Schuurs. 

Below is the order of play, advancement scenarios, match times and breakdowns of the four matches scheduled for Wednesday.

Group Advancement Scenarios

SINGLES
•Rybakina has advanced as the group winner, and the winner between Swiatek and Anisimova will finish second. Keys has been eliminated.
•Rybakina will play the second-place finisher from the Stefanie Graf Group in the semifinals Friday, while Swiatek or Anisimova will face the group winner. 

DOUBLES
•Hsieh-Ostapenko have advanced as the group winner, and the winner between Errani-Paolini and Kudermetova-Mertens will finish second. Muhammad-Schuurs have been eliminated.
•Hsieh-Ostapenko will play the second-place finisher from the Liezel Huber group in the semifinals Friday, while Errani-Paolini or Kudermetova-Mertens will face the group winner. 

Day 5 matchups

Note: All matches are local time.

Sara Errani and Jasmine Paolini (1) vs. Veronika Kudermetova and Elise Mertens (4) — 3 p.m.

It’s a winner-take-all doubles match to start the day, with the second semifinal berth on the line. Top-seeded Errani and Paolini are in danger of not advancing out of the group stage for the second consecutive WTA Finals, and they’ll have their shot to avoid that against familiar faces across the net.

These teams met three times this year, all on clay. Kudermetova and Mertens defeated the Italian duo 6-1, 6-3 in Madrid, before Errani and Paolini avenged the loss in their native Italy, in the Internazionali BNL d’Italia doubles final. 

A few weeks later, the Italians won 6-4, 7-5 in the quarterfinals of Roland Garros en route to their first major doubles title, part of a 14-match win streak. Both teams defeated Muhammad-Schuurs, but fell to Hsieh-Ostapenko in their first two matches in Riyadh. 

Elena Rybakina (6) vs. Madison Keys (7) — Not before 5 p.m.

Head to Head: Tied 3-3

The Case for Rybakina: She’s arguably the best performing player so far in Riyadh. Through two matches, Rybakina has dominated Anisimova, ended a four-match skid against Swiatek and secured the top spot in the group. 

In two previous meetings with Keys this year, Rybakina won in Cincinnati — the first of Keys’ current four-match skid — and lost at the Australian Open, where Keys ultimately won her first Grand Slam. 

The Case for Keys: Just like her first WTA Finals appearance back in 2016, Keys will not advance out of the group stage. The loss to Anisimova eliminated her from qualifying for the semifinals. 

This match is for pride, but a win over Rybakina would also be a huge confidence booster and a nice way to close the 2025 season ahead of next year’s Australian swing. Keys, after being overpowered by Swiatek, took Anisimova to three sets.. 

Keys, currently on a four-match losing streak, hasn’t lost five straight since 2021. 

Iga Swiatek (2) vs. Amanda Anisimova (4) — Not before 6:30 p.m. 

Head to Head: Tied 1-1

The Case for Swiatek: She doesn’t lose back-to-back matches often. In fact, the last time was four years ago at the WTA Finals in Guadalajara, Swiatek’s first appearance at the year-end tournament. 

Swiatek knows how to move on from defeat, and she has the chance to do so against Anisimova. In July, she won the Wimbledon singles title against Anisimova 6-0, 6-0 in just 57 minutes. 

In London, Swiatek won 78% of her first-serve points and 74% of Anisimova’s, breaking serve six times. In the US Open quarterfinal loss, those numbers dropped to 70%, 29% and two, respectively, but Swiatek is vying to avenge that hard-court defeat with a berth to the semifinals on the line.

The Case for Anisimova: One of the biggest storylines from 2025 was Anisimova’s win over Swiatek in the US Open quarterfinals, two months after the defeat at Wimbledon.

Wednesday’s winner-take-all match is essentially a quarterfinal, with the winner advancing to the semifinals.

Anisimova displayed her fight and resilience again on Monday. After a frustrating first set, she defeated Keys 4-6, 6-3, 6-2 in their inaugural meeting, two days after Rybakina outclassed her. 

The first set is crucial for Anisimova’s success. Historically, she’s 3-20 after losing the first set to Top 10 players, and Swiatek is 54-2 in 2025 after winning the first set. (Rybakina handed her one of the two defeats Monday.) Anisimova’s three wins from a set down came against Aryna Sabalenka (Charleston 2022), Paolini (Beijing 2025) and Keys on Monday. 

Hsieh Su-wei and Jelena Ostapenko (6) vs. Asia Muhammad and Demi Schuurs (8)

With a 2-0 start at the WTA Finals and help from the Kudermetova-Mertens win over Muhammad-Schuurs, Hsieh and Ostapenko have clinched the top spot in the group. Even with a win on Wednesday, Muhammad and Schuurs cannot advance.

It will be the first meeting ever between these teams, and though the stakes are lower, Muhammad and Schuurs will be put to the test against a Hsieh-Ostapenko pairing that reached the Australian Open and Wimbledon finals.