Oleksandra Oliynykova vs. McCartney Kessler prediction, odds, picks for Wimbledon 2026

Oleksandra Oliynykova and McCartney Kessler are scheduled to meet in the first round of Wimbledon 2026 on Monday.

Based on the latest simulations, Dimers' advanced tennis model projects McCartney Kessler as the most likely winner of the Oliynykova vs. Kessler match.

This article offers an expanded analysis of Monday's match, including best bets and picks.

Oliynykova vs. Kessler prediction: Who will win and advance to the second round?

Using powerful machine learning and statistical analysis, we have simulated the outcome of Monday's Oliynykova-Kessler women's singles match, forming part of our tennis predictions coverage.

Our leading predictive model gives Kessler an 85% chance of winning against Oliynykova at Wimbledon 2026.

Oleksandra Oliynykova vs. McCartney Kessler odds

We have researched the most up-to-date betting odds in America for this match, which are listed here:

Bet Type	Oliynykova	Kessler
Moneyline	+580	-699
Game Spread	+5.5 (+105)	-5.5 (-165)
Total Games	o19.5 (-110)	u19.5 (-130)

All odds are correct at the time of publication and are subject to change.

Oliynykova vs. Kessler picks and best bet

After matching our probabilities against the best available odds, we can reveal our picks for each of the major markets. Plus, find our best bet for the game below:

Bet Type	Pick	Bet Now
Moneyline	Oliynykova	+580
First Set	Kessler	-130

According to our best tennis bets, the top play to make on this match is Oleksandra Oliynykova to win.

Although Oliynykova is less than likely to win, she provides the best value at the current available odds.

These picks are based on our probabilities matched against the implied probabilities from the sportsbook odds.

Oliynykova vs. Kessler updates and essential details

The Wimbledon 2026 match between Oleksandra Oliynykova and McCartney Kessler is scheduled to start on Monday at 9:20 AM ET.

• Who: Oleksandra Oliynykova vs. McCartney Kessler
• Date: Monday, June 29, 2026
• Approx. Time: 9:20 AM ET/6:20AM PT
• Tournament: Wimbledon Women's Singles 2026
• Round: First round

All dates and times mentioned in this article are United States Eastern Time unless otherwise stated.

Conclusion

We predict McCartney Kessler, with an 85% win probability, will likely beat Oleksandra Oliynykova at Wimbledon 2026.

Additional tools and information for betting safely can be found in our Responsible Gambling hub.