World number 16 Anna Kalinskaya will be up against the 83rd-ranked Caroline Dolehide in the first round of the 2025 Singapore Open which will be played on Monday, January 27. Get all the Anna Kalinskaya v Caroline Dolehide predictions, betting tips and odds for this encounter in the section below.
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Anna Kalinskaya v Caroline Dolehide Head to Head
Their only previous meeting came in the qualifiers of the 2022 Miami Open and Kalinskaya had won that in straight sets.
Kalinskaya Fitness Continues to Frustrate
Anna Kalinskaya hit a career-best ranking of 11th on the WTA charts only last year which is a fair indicator of her quality at the highest level.
What, therefore, would be quite frustrating for both her and her fans is her fitness issues.
She has been known to withdraw from tournaments or retire from matches because of that and that’s been on display all of 2025 too.
After getting knocked out by Ashlyn Krueger in her opener at the Brisbane International, Kalinskaya was forced to retire from her first round match at the Adelaide International against Belinda Bencic.
And she failed to recover in time for her first round match at the Australian Open, allowing lucky loser Eva Lys to take her spot.
The good news for the Russian is that she is back playing and will hope to get her first win of the season under her belt in Singapore.
Dolehide 1-1 in 2025
Once ranked 41st in the world, Caroline Dolehide hasn’t quite gotten going in recent times. Her ranking, as a result, has continued to plummet and she will enter this tournament at 81st on the WTA charts.
Dolehide hasn’t played a lot of tennis this year either, starting out directly at the Australian Open. There she won her opener against 18-year-old and 155th-ranked Sara Bejlek before falling in straight sets to Elina Svitolina.
Interestingly, Dolehide’s career-best performance came in the last tournament she played in 2024 – in Guangzhou – where as a qualifier she made it to the final before losing to Olga Danilovic.
But even that showing had come on the heels of a five-match losing streak.
Kalinskaya v Dolehide Prediction
If Kalinskaya has managed to keep all her fitness woes at bay, she should be the favourite here by some distance. A riskier bet would be for her to win in two but if we are going in with the hypothesis that she is fit, a straight sets win is also likely.
Kalinskaya v Dolehide Tips
- Kalinskaya to win: 2/5
- Kalinskaya to win in straight sets: 11/10
