| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 2024 | Wimbledon | R128 | Mark Lajal | 21 | Estonia |
| 2023 | US Open | R64 | Kaia Kanepi | 38 | Estonia |
| 2023 | Wimbledon | R64 | Anett Kontaveit | 27 | Estonia |
| 2023 | Wimbledon | R128 | Kaia Kanepi | 38 | Estonia |
| 2023 | French Open | R128 | Kaia Kanepi | 37 | Estonia |
| 2023 | French Open | R128 | Anett Kontaveit | 27 | Estonia |
| 2023 | Australian Open | R64 | Anett Kontaveit | 27 | Estonia |
| 2023 | Australian Open | R128 | Kaia Kanepi | 37 | Estonia |
| 2022 | US Open | R64 | Kaia Kanepi | 37 | Estonia |
| 2022 | US Open | R64 | Anett Kontaveit | 26 | Estonia |
| 2022 | Wimbledon | R64 | Anett Kontaveit | 26 | Estonia |
| 2022 | Wimbledon | R128 | Kaia Kanepi | 37 | Estonia |
| 2022 | French Open | R32 | Kaia Kanepi | 36 | Estonia |
| 2022 | French Open | R128 | Anett Kontaveit | 26 | Estonia |
| 2022 | Australian Open | Q | Kaia Kanepi | 36 | Estonia |
| 2022 | Australian Open | R64 | Anett Kontaveit | 26 | Estonia |
| 2021 | US Open | R32 | Anett Kontaveit | 25 | Estonia |
| 2021 | US Open | R64 | Kaia Kanepi | 36 | Estonia |
| 2021 | Wimbledon | R128 | Anett Kontaveit | 25 | Estonia |
| 2021 | Wimbledon | R128 | Kaia Kanepi | 36 | Estonia |
| 2021 | French Open | R32 | Anett Kontaveit | 25 | Estonia |
| 2021 | French Open | R128 | Kaia Kanepi | 35 | Estonia |
| 2021 | Australian Open | R32 | Anett Kontaveit | 25 | Estonia |
| 2021 | Australian Open | R32 | Kaia Kanepi | 35 | Estonia |
| 2020 | French Open | R64 | Kaia Kanepi | 35 | Estonia |
| 2020 | French Open | R128 | Anett Kontaveit | 24 | Estonia |
| 2020 | US Open | R16 | Anett Kontaveit | 24 | Estonia |
| 2020 | US Open | R64 | Kaia Kanepi | 35 | Estonia |
| 2020 | Australian Open | Q | Anett Kontaveit | 24 | Estonia |
| 2020 | Australian Open | R128 | Kaia Kanepi | 34 | Estonia |
| 2019 | US Open | R32 | Anett Kontaveit | 23 | Estonia |
| 2019 | US Open | R64 | Kaia Kanepi | 34 | Estonia |
| 2019 | Wimbledon | R32 | Anett Kontaveit | 23 | Estonia |
| 2019 | Wimbledon | R64 | Kaia Kanepi | 34 | Estonia |
| 2019 | French Open | R16 | Kaia Kanepi | 33 | Estonia |
| 2019 | French Open | R128 | Anett Kontaveit | 23 | Estonia |
| 2019 | Australian Open | R64 | Anett Kontaveit | 23 | Estonia |
| 2019 | Australian Open | R128 | Kaia Kanepi | 33 | Estonia |
| 2018 | US Open | R16 | Kaia Kanepi | 33 | Estonia |
| 2018 | US Open | R128 | Anett Kontaveit | 22 | Estonia |
| 2018 | Wimbledon | R32 | Anett Kontaveit | 22 | Estonia |
| 2018 | Wimbledon | R128 | Kaia Kanepi | 33 | Estonia |
| 2018 | French Open | R16 | Anett Kontaveit | 22 | Estonia |
| 2018 | French Open | R32 | Jürgen Zopp | 30 | Estonia |
| 2018 | French Open | R128 | Kaia Kanepi | 32 | Estonia |
| 2018 | Australian Open | R16 | Anett Kontaveit | 22 | Estonia |
| 2018 | Australian Open | R32 | Kaia Kanepi | 32 | Estonia |
| 2017 | US Open | Q | Kaia Kanepi | 32 | Estonia |
| 2017 | US Open | R128 | Anett Kontaveit | 21 | Estonia |
| 2017 | Wimbledon | R32 | Anett Kontaveit | 21 | Estonia |
Open Era Grand Slam Tennis