World No. 4 Amanda Anisimova will face seventh-ranked Madison Keys in her second round-robin stage match at the 2025 WTA Finals on Monday, November 3. In her first-ever appearance at the year-end championships on Saturday, Anisimova struggled quite a lot as she lost 3-6, 1-6 to Elena Rybakina in less than an hour.
Keys, meanwhile, also got blanked by 2023 champion Iga Świątek in her first match of the Serena Williams Group, going out 1-6, 2-6 in just over an hour. The reigning Australian Open champion is now on a three-match losing streak. However, it is essential to note that a wrist injury had put her out of action following the US Open, contributing to her lack of match practice.
Amanda Anisimova vs Madison Keys Match Details
Date: Nov. 3, 2025
Tournament: WTA Finals 2025
Round: Round-robin
Venue: King Saud University Indoor Arena, Riyadh, Saudi Arabia
Category: WTA Finals
Surface: Indoor Hardcourt
Live Telecast: Tennis Channel, TSN, Sky Sports
Anisimova vs Keys Head-to-Head
Amanda Anisimova and Madison Keys have never faced off on the WTA Tour, despite both players’ careers overlapping since 2019. Therefore, their head-to-head record stands at 0-0.
Anisimova vs Keys Prediction
For what it’s worth, Amanda Anisimova was blown away by a stellar performance from Rybakina earlier on Saturday. The 24-year-old won 56% (19/34) of her first-serve points, which wasn’t too far off from her 2025 tour-level average of 66.1%. The WTA Finals debutant will likely play much more freely in her second round-robin match, since she would’ve become accustomed to the playing conditions at the King Saud Arena.
More importantly, the American’s aggressive style of play matches up well against her compatriot, who also swats virtually every shot she hits from either wing. The US Open finalist’s backhand, in particular, is one of her biggest weapons. However, Madison Keys has a great running forehand that can counteract her opponent’s backhand.
Although the 30-year-old is herself a respectable server, it is her return prowess and unpredictability during rallies that set her apart from the rest of the WTA Tour. And just like Anisimova, she is likely to have shaken off her rust and will feel more at home in terms of her game on Sunday.
The keys to winning this match for both players will be to maintain a healthy winners-to-unforced errors ratio and hit a high percentage of first serves. Madison Keys has won 67.8% of her first-serve points and is generally more dependable during her service games, giving her a slight edge in this all-American clash at the 2025 WTA Finals.
Prediction: Madison Keys to win in three sets.