H2H data updated: 2026-09-13 00:00 UTC
Anna Kalinskaya holds a 1–0 lead over Robin Montgomery in their WTA head-to-head. Across 1 main-draw meeting, Anna Kalinskaya leads 1–0 on hard courts. Most recently, Anna Kalinskaya won the 2022 Miami Open first round 4-6 6-4 7-6(4).
Want to explore more matchups? Advanced rivalry search lets you browse current and historical rivalries, unbeaten records, or every matchup for a player.
| Player | Score | Player | Match Data | Date | Round | Tournament | Category | Surface |
|---|---|---|---|---|---|---|---|---|
| Anna Kalinskaya | 4-6 6-4 7-6(4) | Robin Montgomery | Match data | Mar 24, 2022* | R128 | Miami Open | WTA 1000 | Hard |
Estimated match date where the exact historical date is unavailable. Arrows show an edition's recorded category and documented modern equivalent; unresolved editions keep their recorded category. Asterisked totals include editions mapped from documented historical predecessor categories. Mapping details.
| Player | Current | Peak | Pts | Elo | W | L | Win % | GS | 1000 including documented historical predecessor categories | Finals | 500 including documented historical predecessor categories | 250 including documented historical predecessor categories | Titles |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Anna Kalinskaya | #23 | #11 | 2,975 | 1,956 | 141 | 127 | 52.6% | 0 | 0 | 0 | 0 | 0 | 0 |
| Robin Montgomery | #187 | #95 | 741 | 1,767 | 19 | 26 | 42.2% | 0 | 0 | 0 | 0 | 1 | 1 |
Seasons are aligned by the age each player spent most of that calendar year. GS and Titles are cumulative career totals through that season.
| Age | Anna Kalinskaya | Robin Montgomery | ||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Yr | W-L | Win % | Rank | Elo | GS | Titles | Yr | W-L | Win % | Rank | Elo | GS | Titles | |
| 15 | — | — | — | — | — | — | — | 2020 | 0–1 | 0.0% | #413 | 1,474 | 0 | 0 |
| 16 | — | — | — | — | — | — | — | 2021 | 0–1 | 0.0% | #372 | 1,466 | 0 | 0 |
| 17 | 2016 | 0–1 | 0.0% | #186 | 1,479 | 0 | 0 | 2022 | 0–3 | 0.0% | #219 | 1,522 | 0 | 0 |
| 18 | 2017 | 3–6 | 33.3% | #161 | 1,529 | 0 | 0 | 2023 | 1–4 | 20.0% | #191 | 1,569 | 0 | 0 |
| 19 | 2018 | 0–8 | 0.0% | #166 | 1,461 | 0 | 0 | 2024 | 7–8 | 46.7% | #117 | 1,626 | 0 | 0 |
| 20 | 2019 | 7–7 | 50.0% | #105 | 1,599 | 0 | 0 | 2025 | 6–5 | 54.5% | #212 | 1,657 | 0 | 0 |
| 21 | 2020 | 1–6 | 14.3% | #114 | 1,598 | 0 | 0 | 2026 | 5–4 | 55.6% | #187 | 1,753 | 0 | 1 |
| 22 | 2021 | 12–14 | 46.2% | #111 | 1,725 | 0 | 0 | — | — | — | — | — | — | — |
| 23 | 2022 | 17–15 | 53.1% | #58 | 1,811 | 0 | 0 | — | — | — | — | — | — | — |
| 24 | 2023 | 16–13 | 55.2% | #76 | 1,819 | 0 | 0 | — | — | — | — | — | — | — |
| 25 | 2024 | 33–19 | 63.5% | #14 | 1,893 | 0 | 0 | — | — | — | — | — | — | — |
| 26 | 2025 | 25–20 | 55.6% | #33 | 1,888 | 0 | 0 | — | — | — | — | — | — | — |
| 27 | 2026 | 27–18 | 60.0% | #23 | 1,930 | 0 | 0 | — | — | — | — | — | — | — |
Seasons are aligned by the age each player spent most of that calendar year. Results cover completed main-draw matches. Bold green marks the higher win percentage when both players have at least 5 matches on that surface at the aligned age.
| Age | Anna Kalinskaya | Robin Montgomery | ||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Yr | Hard | Clay | Grass | Yr | Hard | Clay | Grass | |||||||||||||||||||
| W | L | M | Win % | W | L | M | Win % | W | L | M | Win % | W | L | M | Win % | W | L | M | Win % | W | L | M | Win % | |||
| 15 | — | — | — | — | — | — | — | — | — | — | — | — | — | 2020 | 0 | 1 | 1 | 0.0% | — | — | — | — | — | — | — | — |
| 16 | — | — | — | — | — | — | — | — | — | — | — | — | — | 2021 | 0 | 1 | 1 | 0.0% | — | — | — | — | — | — | — | — |
| 17 | 2016 | 0 | 1 | 1 | 0.0% | — | — | — | — | — | — | — | — | 2022 | 0 | 3 | 3 | 0.0% | — | — | — | — | — | — | — | — |
| 18 | 2017 | 1 | 2 | 3 | 33.3% | 2 | 2 | 4 | 50.0% | 0 | 2 | 2 | 0.0% | 2023 | 1 | 4 | 5 | 20.0% | — | — | — | — | — | — | — | — |
| 19 | 2018 | 0 | 4 | 4 | 0.0% | 0 | 3 | 3 | 0.0% | 0 | 1 | 1 | 0.0% | 2024 | 2 | 4 | 6 | 33.3% | 2 | 2 | 4 | 50.0% | 3 | 2 | 5 | 60.0% |
| 20 | 2019 | 7 | 5 | 12 | 58.3% | — | — | — | — | 0 | 2 | 2 | 0.0% | 2025 | 4 | 2 | 6 | 66.7% | 2 | 3 | 5 | 40.0% | — | — | — | — |
| 21 | 2020 | 1 | 5 | 6 | 16.7% | 0 | 1 | 1 | 0.0% | — | — | — | — | 2026 | 0 | 1 | 1 | 0.0% | 0 | 2 | 2 | 0.0% | 5 | 1 | 6 | 83.3% |
| 22 | 2021 | 11 | 9 | 20 | 55.0% | 1 | 3 | 4 | 25.0% | 0 | 2 | 2 | 0.0% | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 23 | 2022 | 14 | 8 | 22 | 63.6% | 1 | 4 | 5 | 20.0% | 2 | 3 | 5 | 40.0% | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 24 | 2023 | 9 | 10 | 19 | 47.4% | 7 | 3 | 10 | 70.0% | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 25 | 2024 | 24 | 13 | 37 | 64.9% | 2 | 4 | 6 | 33.3% | 7 | 2 | 9 | 77.8% | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 26 | 2025 | 19 | 15 | 34 | 55.9% | 5 | 4 | 9 | 55.6% | 1 | 1 | 2 | 50.0% | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 27 | 2026 | 16 | 11 | 27 | 59.3% | 8 | 4 | 12 | 66.7% | 3 | 3 | 6 | 50.0% | — | — | — | — | — | — | — | — | — | — | — | — | — |
| Career | — | 102 | 83 | 185 | 55.1% | 26 | 28 | 54 | 48.1% | 13 | 16 | 29 | 44.8% | — | 7 | 16 | 23 | 30.4% | 4 | 7 | 11 | 36.4% | 8 | 3 | 11 | 72.7% |
Seasons are aligned by the age each player spent most of that calendar year. Detailed serve and return statistics available for 253/268 of Anna Kalinskaya's and 39/45 of Robin Montgomery's main draw matches. Sample is shown as matches with detailed serve and return statistics / total main draw matches. Bold green marks the stronger value when both stat samples contain at least 5 matches; lower is better for DFs/M.
| Age | Anna Kalinskaya | Robin Montgomery | ||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Yr | Sample | Aces/M | DFs/M | 1st Sv% | 1st Pts% | 2nd Pts% | BP Saved% | BP Conv% | Svc Pts% | Ret Pts% | Yr | Sample | Aces/M | DFs/M | 1st Sv% | 1st Pts% | 2nd Pts% | BP Saved% | BP Conv% | Svc Pts% | Ret Pts% | |
| 15 | — | —/— | — | — | — | — | — | — | — | — | — | 2020 | 1/1 | 2.0 | 4.0 | 66.7% | 43.3% | 20.0% | 14.3% | 40.0% | 35.6% | 39.1% |
| 16 | — | —/— | — | — | — | — | — | — | — | — | — | 2021 | 1/1 | 3.0 | 7.0 | 50.8% | 67.7% | 30.0% | 33.3% | 33.3% | 49.2% | 36.0% |
| 17 | — | —/— | — | — | — | — | — | — | — | — | — | 2022 | 3/3 | 3.3 | 7.0 | 58.0% | 59.7% | 42.6% | 39.3% | 32.5% | 52.3% | 36.1% |
| 18 | 2017 | 9/9 | 1.4 | 4.1 | 62.4% | 62.9% | 42.7% | 36.2% | 35.2% | 55.6% | 42.0% | 2023 | 5/5 | 4.4 | 7.8 | 57.1% | 64.7% | 34.1% | 51.2% | 48.0% | 51.8% | 30.5% |
| 19 | 2018 | 8/8 | 1.4 | 5.0 | 61.1% | 51.5% | 38.3% | 40.8% | 23.9% | 46.6% | 37.7% | 2024 | 14/15 | 4.7 | 5.8 | 63.7% | 67.5% | 43.0% | 55.7% | 37.6% | 58.7% | 37.4% |
| 20 | 2019 | 14/14 | 1.6 | 4.3 | 60.3% | 61.3% | 43.6% | 54.5% | 43.2% | 54.2% | 40.1% | 2025 | 7/11 | 3.9 | 5.3 | 66.2% | 64.1% | 40.7% | 47.1% | 50.4% | 56.3% | 42.6% |
| 21 | 2020 | 7/7 | 1.6 | 3.6 | 64.7% | 56.7% | 46.6% | 45.0% | 60.5% | 53.3% | 33.0% | 2026 | 8/9 | 6.3 | 3.6 | 65.0% | 67.7% | 39.9% | 58.1% | 53.5% | 58.3% | 42.5% |
| 22 | 2021 | 26/26 | 1.2 | 4.0 | 63.4% | 58.7% | 47.2% | 49.6% | 40.3% | 54.7% | 40.6% | — | —/— | — | — | — | — | — | — | — | — | — |
| 23 | 2022 | 31/32 | 1.5 | 4.6 | 61.5% | 64.1% | 44.9% | 56.9% | 42.0% | 56.6% | 41.7% | — | —/— | — | — | — | — | — | — | — | — | — |
| 24 | 2023 | 29/29 | 1.9 | 3.4 | 64.7% | 64.6% | 46.1% | 53.5% | 55.6% | 57.9% | 44.3% | — | —/— | — | — | — | — | — | — | — | — | — |
| 25 | 2024 | 50/52 | 1.8 | 3.7 | 66.6% | 64.1% | 49.7% | 57.5% | 48.7% | 59.2% | 45.2% | — | —/— | — | — | — | — | — | — | — | — | — |
| 26 | 2025 | 36/46 | 2.5 | 4.1 | 64.8% | 64.7% | 46.0% | 52.4% | 47.9% | 58.4% | 41.3% | — | —/— | — | — | — | — | — | — | — | — | — |
| 27 | 2026 | 43/45 | 2.3 | 4.5 | 61.5% | 64.0% | 46.6% | 47.7% | 51.8% | 57.0% | 44.5% | — | —/— | — | — | — | — | — | — | — | — | — |
| Career | — | 253/269 | 1.8 | 4.1 | 63.6% | 62.9% | 46.4% | 52.0% | 47.0% | 56.8% | 42.5% | — | 39/45 | 4.6 | 5.6 | 62.9% | 65.4% | 39.8% | 51.2% | 44.1% | 56.0% | 38.4% |
Seasons are aligned by the age each player spent most of that calendar year. Metrics use eligible main-draw results; point statistics use matches with detailed data. Bold green marks the stronger value when both underlying samples are sufficient. Lower is better for Schedule because a negative value means a tougher schedule. Career Schedule is normalized per 100 matches.
| Age | Anna Kalinskaya | Robin Montgomery | ||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Yr | Elo | P+ | Serve+ | Return+ | PD | TPW% | Hard Elo | Clay Elo | Grass Elo | Set Win % | Set Margin | Dec. Set | Tiebreak | Pressure+ | Schedule | Yr | Elo | P+ | Serve+ | Return+ | PD | TPW% | Hard Elo | Clay Elo | Grass Elo | Set Win % | Set Margin | Dec. Set | Tiebreak | Pressure+ | Schedule | |
| 14 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | 2019 | 1488 | 99.9 | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 15 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | 2020 | 1474 | 101.9 | -0.63 | -1.27 | 0.607 | 37.4% | — | — | — | 0.0% | -4.00 | — | — | — | -0.07 |
| 16 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | 2021 | 1467 | 107.9 | -0.59 | +1.33 | 0.708 | 41.9% | — | — | — | 33.3% | -2.67 | 0–1 | — | — | -0.05 |
| 17 | 2016 | 1480 | 99.5 | — | — | — | — | — | — | — | 0.0% | -3.00 | — | — | — | -0.05 | 2022 | 1522 | 121.8 | -0.75 | -0.37 | 0.758 | 44.4% | +13 | — | — | 14.3% | -1.86 | 0–1 | 0–1 | — | -0.26 |
| 18 | 2017 | 1530 | 103.2 | -0.33 | -0.89 | 0.947 | 48.2% | -31 | +19 | — | 35.0% | -0.65 | 1–1 | 0–2 | — | -0.05 | 2023 | 1570 | 105.8 | -0.95 | -3.60 | 0.632 | 42.1% | -44 | — | — | 25.0% | -2.00 | 1–1 | 1–1 | — | +0.05 |
| 19 | 2018 | 1462 | 106.4 | -4.83 | -2.18 | 0.705 | 42.3% | -30 | +83 | — | 11.1% | -2.89 | 0–2 | 1–0 | — | -0.33 | 2024 | 1626 | 120.6 | +0.52 | -2.28 | 0.905 | 48.2% | -48 | -25 | +224 | 47.1% | -0.56 | 2–4 (33%) | 1–2 (33%) | — | +0.12 |
| 20 | 2019 | 1599 | 113.0 | -1.49 | -2.24 | 0.876 | 47.3% | -7 | — | — | 45.5% | -0.70 | 4–1 (80%) | 1–1 | — | +0.73 | 2025 | 1658 | 125.8 | -0.81 | -0.51 | 0.975 | 49.6% | -40 | -59 | — | 53.8% | +0.54 | 2–2 (50%) | — | — | +0.27 |
| 21 | 2020 | 1598 | 114.2 | -1.46 | -3.46 | 0.706 | 43.4% | +5 | — | — | 14.3% | -2.00 | — | 0–1 | — | +0.11 | 2026 | 1754 | 119.3 | +0.53 | -0.95 | 1.020 | 50.3% | — | — | +248 | 52.6% | +0.37 | 1–2 (33%) | 1–0 | — | -0.17 |
| 22 | 2021 | 1726 | 126.0 | -0.98 | -2.00 | 0.896 | 47.8% | +26 | -238 | — | 48.3% | -0.37 | 5–5 (50%) | 4–2 (67%) | 102.5 | -0.36 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 23 | 2022 | 1811 | 133.4 | +0.35 | -0.59 | 0.961 | 49.2% | +71 | -374 | -298 | 59.0% | +0.10 | 7–6 (54%) | 6–1 (86%) | 105.8 | -1.11 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 24 | 2023 | 1820 | 137.4 | +0.79 | +1.49 | 1.053 | 51.1% | -14 | -185 | — | 59.7% | +0.40 | 5–8 (38%) | 6–1 (86%) | 102.3 | -1.35 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 25 | 2024 | 1894 | 153.5 | +2.49 | +2.47 | 1.109 | 52.2% | +28 | -284 | -109 | 62.2% | +0.85 | 10–9 (53%) | 7–6 (54%) | 101.5 | +0.71 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 26 | 2025 | 1888 | 147.6 | +1.57 | -0.62 | 0.993 | 49.9% | +7 | -198 | — | 51.9% | +0.12 | 10–4 (71%) | 11–5 (69%) | 109.3 | -1.32 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — |
| 27 | 2026 | 1930 | 152.9 | +0.96 | +1.72 | 1.035 | 50.5% | +3 | -106 | -172 | 56.6% | +0.15 | 10–6 (63%) | 9–4 (69%) | 108.0 | -0.30 | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — | — |
| Career | — | 1957 | 142.5 | +0.62 | +0.26 | 0.986 | 49.7% | +16 | -172 | -175 | 52.7% | +0.02 | 52–42 (55%) | 45–23 (66%) | 114.3 | -1.25 | — | 1767 | 124.9 | -0.06 | -1.59 | 0.872 | 47.4% | -35 | -44 | +237 | 43.7% | -0.50 | 6–11 (35%) | 3–4 (43%) | 98.3 | -0.26 |
Each player's five most-played main-draw opponents. The current matchup is highlighted when it appears in a player's top five.
| Opponent | W | L | M | Last Played | H2H |
|---|---|---|---|---|---|
| Elina Svitolina | 2 | 4 | 6 | Sep 5, 2026 | H2H |
| Jessica Pegula | 1 | 5 | 6 | Jul 31, 2026 | H2H |
| Belinda Bencic | 1 | 5 | 6 | Jul 3, 2026 | H2H |
| Daria Kasatkina | 2 | 3 | 5 | Jul 28, 2026 | H2H |
| Jelena Ostapenko | 4 | 1 | 5 | May 11, 2026 | H2H |
| Opponent | W | L | M | Last Played | H2H |
|---|---|---|---|---|---|
| Magda Linette | 1 | 2 | 3 | Apr 21, 2026 | H2H |
| Jule Niemeier | 2 | 0 | 2 | Mar 6, 2025 | H2H |
| Ons Jabeur | 1 | 1 | 2 | Aug 2, 2024 | H2H |
| Maria Sakkari | 0 | 1 | 1 | Sep 1, 2026 | H2H |
| Jasmine Paolini | 0 | 1 | 1 | Jun 30, 2026 | H2H |