Chicago Fall Tennis Classic 2021: Anett Kontaveit vs Madison Brengle preview, head-to-head & prediction

Match details

Fixture: (11) Anett Kontaveit vs Madison Brengle

Date: 28 September 2021

Tournament: Chicago Fall Tennis Classic 2021

Round: First round (Round of 64)

Venue: Chicago, USA

Category: WTA 500

Surface: Hardcourt

Prize money: $565,530

Live telecast: USA - Tennis Channel & ESPN | UK - Amazon Prime Video

Anett Kontaveit vs Madison Brengle preview

11th seed Anett Kontaveit will kick off her campaign in Chicago against America's Madison Brengle.

Kontaveit's season has been quite up and down so far. Her performance at the Slams and the WTA 1000 events has been dismal, as she has failed to progress beyond the third round at any of them. However, the Estonian has been quite successful at the lower level events.

She has been in particularly fine form over the past month, winning two titles in this period. The 25-year-old won the WTA 500 in Ostrava just last weekend without dropping a set, defeating quality players like Maria Sakkari and Petra Kvitova along the way.

Kontaveit will also have an eye on the race to the WTA Finals. A strong finish in Chicago could solidify her chances of qualifying for the event for the very first time.

Madison Brengle in action at the 2021 Yarra Valley Classic.

Madison Brengle, meanwhile, has been oscillating between the WTA tour and the ITF circuit for a long time. Her best result on the main tour this year has been reaching the third round of Wimbledon, defeating former Slam champion Sofia Kenin along the way. Aside from that, however, the American has lost in the first couple of rounds at every tournament she has played.

Brengle has been a little more successful at the ITF level, reaching the final of the ITF event in Charleston earlier this year.

Anett Kontaveit vs Madison Brengle head-to-head

Anett Kontaveit and Madison Brengle have faced each other thrice, with Kontaveit currently leading the head-to-head 3-0. But their most recent encounter was more than three years ago, at Roland Garros 2018, where the Estonian earned a hard-fought three-set win.

Anett Kontaveit vs Madison Brengle preview

Anett Kontaveit won her second title of the year in Ostrava.

Given their current form and the contrasting levels they've played at this year, Anett Kontaveit is the overwhelming favorite to win this match. However, Madison Brengle is a dogged counterpuncher who loves to engage in lengthy battles. That could cause Kontaveit a few problems, especially since she might be a little fatigued from her Ostrava run.

The American has troubled Kontaveit in the past, with two of their three matches going the distance. But it is likelt that the Estonian, who loves to dictate play from the baseline with her aggressive groundstrokes, will have enough in the tank to hit through her opponent for another win.

Prediction: Anett Kontaveit to win in three sets.