Robin Montgomery and Caroline Dolehide will play each other in the qualifications of Wimbledon for the 1st time in their career. They are scheduled to play on Tuesday at 5:00 pm on COURT 16. Here the head to head stats and relative prediction.
Prediction, odds and live streaming
The pick for Tennis Tonic is Robin Montgomery who should win in 2 sets.
As per the initial odds, Robin Montgomery is the pick to win this match.
Robin Montgomery -> 1.36
Caroline Dolehide -> 3
Here where top tennis events are broadcasted or streamed online (ATP, WTA).
At the challenger level, there will be free live streaming on Challenger TV.
Prediction and head to head Robin Montgomery vs. Caroline Dolehide
There is no head to head record between Robin Montgomery and Caroline Dolehide since this will be the first time that they will square off in the main tour.
Robin Montgomery
| Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2026 | 19-11 | 5-3 | 5-7 | 0-0 | 9-1 | 0-0 |
| 2025 | 12-9 | 6-4 | 2-3 | 0-0 | 4-2 | 0-0 |
| 2024 | 35-23 | 9-9 | 14-10 | 2-1 | 10-3 | 0-0 |
| 2023 | 26-22 | 11-11 | 10-8 | 1-1 | 4-2 | 0-0 |
| 2022 | 36-16 | 23-12 | 4-2 | 9-2 | 0-0 | 0-0 |
Ranked no. 194, Montgomery will start her run in Wimbledon after she won the title in Hertogenbosch after beating w/o Krejcikova in the final.
Montgomery has a composed 11-7 win-loss record in 2026, 6-0 on grass (See FULL STATS).
Her best result of the current season was conquering the title in Hertogenbosch where she defeated Barbora Krejcikova in the final w/o.
Montgomery won her last 6 matches.
Talking about her overall career, Robin has an overall 144-95 record. She has a positive 24-7 record on grass.
Previously in Wimbledon
Previously, her best result was reaching the 2nd round in 2024. See her history.
Caroline Dolehide
5 - 5win/loss
207
41
LWWWLLLWWL | Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2026 | 15-12 | 13-8 | 2-2 | 0-0 | 0-2 | 0-0 |
| 2025 | 25-27 | 13-15 | 9-7 | 1-2 | 2-3 | 0-0 |
| 2024 | 20-27 | 14-18 | 3-4 | 0-0 | 3-5 | 0-0 |
| 2023 | 45-24 | 21-13 | 24-8 | 0-0 | 0-3 | 0-0 |
| 2022 | 27-26 | 20-15 | 7-9 | 0-0 | 0-2 | 0-0 |
Ranked no. 215, Dolehide will start her run in London after she played her last match in Bogota where she lost 6-7(5) 6-2 6-1 to Camila Osorio Serrano in the 1st round on the 31st of March.
Caroline has a composed 5-5 win-loss record in 2026, 0-0 on grass (See FULL STATS).
This will be the first match of the year on grass.
In terms of her career, Caroline has an overall 302-241 record. She has a negative 16-25 record on grass.
Previously in Wimbledon
Previously, her best result was reaching the 2nd round in 2025. See her history.
Head 2 Head
WWWWWWWWWW
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