Level, 2 wins each over 4 singles meetings since 2022. Last meeting on 24/06/2026 at Wimbledon - London.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 24/06/2026 | Wimbledon - London | Qualifying 2 | grass | Montgomery | 6-2 6-2 |
| 07/04/2026 | Grand Prix Open Villa de Madrid - Madrid | Round 1 | clay | Kalieva | 6-4 4-6 4-6 |
| 26/02/2023 | ATX Open - Austin | Qualifiers | hard | Montgomery | 7-6(4) 6-1 |
| 06/10/2022 | W80 Rancho Santa Fe | Round 2 | hard | Kalieva | 2-6 6-2 6-6 |
| grass | Kalieva 0 - 1 Montgomery |
| clay | Kalieva 1 - 0 Montgomery |
| hard | Kalieva 1 - 1 Montgomery |
| 2026 | Kalieva 1 - 1 Montgomery |
| 2023 | Kalieva 0 - 1 Montgomery |
| 2022 | Kalieva 1 - 0 Montgomery |
186 wins, 157 losses since 2021 (54.2%).
Last matches: D V V V D
133 wins, 84 losses since 2021 (61.3%).
Last matches: D V V V D
Level, 2 wins each over 4 singles meetings since 2022.
On 24/06/2026, at Wimbledon - London (Qualifying 2): Robin Montgomery won 6-2 6-2.