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| Semi-finals | Riera J. | Montgomery R. | 2:1 (2:6, 6:2, 6:1) | dettagli | 20.05.2026 | ||
| Quarter-finals | Montgomery R. | Inglis M. | 2:0 (6:1, 7:5) | dettagli | 19.05.2026 | ||
| 1/8-finals | Montgomery R. | Oz I. | 0:2 (2:6, 3:6) | dettagli | 07.05.2026 | ||
| 1/16-finals | Leonard M. | Montgomery R. | 1:2 (6:4, 3:6, 1:6) | dettagli | 06.05.2026 | ||
| 1/64-finals | Montgomery R. | Linette M. | 0:2 (4:6, 3:6) | dettagli | 21.04.2026 | ||
| Semi-finals | Chwalinska M. | Montgomery R. | 2:0 (6:2, 6:0) | dettagli | 18.04.2026 | ||
| Quarter-finals | Lamens S. | Montgomery R. | 1:2 (4:6, 6:3, 4:6) | dettagli | 17.04.2026 | ||
| 1/8-finals | Koevermans A. | Montgomery R. | 0:2 (4:6, 67:7) | dettagli | 15.04.2026 | ||
| 1/16-finals | Montgomery R. | Sherif M. | 2:1 (3:6, 7:5, 7:67) | dettagli | 13.04.2026 | ||
| 1/16-finals | Montgomery R. | Kalieva E. | 1:2 (6:4, 4:6, 4:6) | dettagli | 07.04.2026 | ||
| 1/16-finals | Montgomery R. | Blinkova A. | 0:2 (2:6, 3:6) | dettagli | 31.03.2026 | ||
| Final | Montgomery R. | Juvan K. | 0:2 (3:6, 67:7) | dettagli | 26.06.2025 | ||
| Semi-finals | Montgomery R. | Tig P. M. | 2:0 (6:4, 6:2) | dettagli | 25.06.2025 | ||
| Quarter-finals | Montgomery R. | Vandewinkel H. | 2:1 (7:66, 63:7, 6:3) | dettagli | 24.06.2025 | ||
| Semi-finals | Wickmayer Y. | Montgomery R. | CAN. | dettagli | 07.06.2025 | ||
| Quarter-finals | Masarova R. | Montgomery R. | 1:0 RET. (6:2) | dettagli | 06.06.2025 | ||
| 1/8-finals | Montgomery R. | Sonmez Z. | 2:1 (7:66, 4:6, 6:4) | dettagli | 06.06.2025 | ||
| 1/16-finals | Montgomery R. | Gibson T. | 2:1 (6:4, 2:6, 7:61) | dettagli | 03.06.2025 | ||
| 1/32-finals | Montgomery R. | Bouzas Maneiro J. | 1:2 (4:6, 6:4, 5:7) | dettagli | 29.05.2025 | ||
| 1/64-finals | Parry D. | Montgomery R. | 0:2 (2:6, 1:6) | dettagli | 26.05.2025 | ||
| 1/64-finals | Uchijima M. | Montgomery R. | 2:1 (1:6, 6:4, 6:3) | dettagli | 23.04.2025 | ||
| 1/16-finals | Montgomery R. | Collins D. | 0:2 (3:6, 1:6) | dettagli | 02.04.2025 | ||
| 1/32-finals | Tomova V. | Montgomery R. | 0:2 (1:6, 3:6) | dettagli | 31.03.2025 | ||
| Final | Pera B. | Montgomery R. | 2:0 (7:62, 6:4) | dettagli | 17.03.2025 | ||
| Semi-finals | Pedone G. | Montgomery R. | 0:2 (2:6, 0:6) | dettagli | 16.03.2025 | ||
| 1/32-finals | Kostyuk M. | Montgomery R. | 2:0 (6:1, 6:3) | dettagli | 07.03.2025 | ||
| 1/64-finals | Niemeier J. | Montgomery R. | 1:2 (6:3, 5:7, 2:6) | dettagli | 06.03.2025 | ||
| Semi-finals | Montgomery R. | Stojanovic N. | 1:2 (4:6, 7:65, 3:6) | dettagli | 08.01.2025 | ||
| Quarter-finals | Montgomery R. | Hercog P. | 2:0 (6:2, 6:1) | dettagli | 07.01.2025 | ||
| Semi-finals | Tauson C. | Montgomery R. | 2:0 (6:4, 6:3) | dettagli | 04.01.2025 | ||
| Quarter-finals | Pera B. | Montgomery R. | 0:2 (4:6, 4:6) | dettagli | 03.01.2025 | ||
| 1/8-finals | Hibino N. | Montgomery R. | 0:2 (2:6, 2:6) | dettagli | 02.01.2025 | ||
| 1/16-finals | Montgomery R. | Raducanu E. | CAN. | dettagli | 31.12.2024 | ||
| 1/16-finals | Montgomery R. | Hontama M. | 2:1 (6:3, 2:6, 6:0) | dettagli | 31.12.2024 | ||
| 1/16-finals | Montgomery R. | Bejlek S. | 1:2 (7:5, 63:7, 1:6) | dettagli | 26.11.2024 | ||
| 1/8-finals | Montgomery R. | Maristany G. | 0:2 (0:6, 1:6) | dettagli | 21.11.2024 | ||
| 1/16-finals | Montgomery R. | In-Albon Y. | 2:0 (6:3, 6:4) | dettagli | 19.11.2024 | ||
| 1/16-finals | Montgomery R. | Sierra S. | CAN. | dettagli | 19.11.2024 | ||
| 1/8-finals | Smith T. N. | Montgomery R. | 2:0 (6:3, 6:3) | dettagli | 06.11.2024 | ||
| 1/16-finals | Perez Garcia M. P. | Montgomery R. | 0:2 (3:6, 0:6) | dettagli | 04.11.2024 | ||
| 1/16-finals | Montgomery R. | Jacquemot E. | 1:2 (6:4, 3:6, 64:7) | dettagli | 28.10.2024 | ||
| 1/8-finals | Eikeri U./Gleason Q. | Gauff C./Montgomery R. | WO. | dettagli | 26.04.2026 | ||
| 1/16-finals | Gauff C./Montgomery R. | Khromacheva I./Olmos G. | 2:0 (6:3, 6:4) | dettagli | 23.04.2026 | ||
| 1/8-finals | Erjavec V./Mladenovic K. | Montgomery R./Osuigwe W. | 2:0 (6:3, 6:2) | dettagli | 15.04.2026 | ||
| 1/8-finals | Montgomery R./Osuigwe W. | Brooks M./Corley I. | 0:2 (3:6, 64:7) | dettagli | 06.04.2026 | ||
| 1/8-finals | Fruhvirtova L./Montgomery R. | Golubic V./Minnen G. | CAN. | dettagli | 03.06.2025 | ||
| Quarter-finals | Azarenka V./Krueger A. | Gauff C./Montgomery R. | 2:0 (7:65, 6:3) | dettagli | 29.04.2025 | ||
| 1/8-finals | Hunter S./Perez E. | Gauff C./Montgomery R. | 0:2 (4:6, 3:6) | dettagli | 27.04.2025 | ||
| 1/16-finals | Gauff C./Montgomery R. | Dolehide C./Krawczyk D. | 2:0 (6:3, 6:0) | dettagli | 25.04.2025 | ||
| 1/16-finals | Andreeva M./Shnaider D. | Kessler M./Montgomery R. | 2:1 (67:7, 6:4, 10:5) | dettagli | 20.03.2025 | ||