| TT Cup (2023) | 07/12 08:45 | - | Martin Pakk v Kalle Kask | L | 3-1 | |
| TT Cup (2023) | 07/12 07:45 | - | Yuto Kobayashi v Kalle Kask | L | 3-1 | |
| TT Cup (2023) | 07/12 07:15 | - | Martin Pakk v Kalle Kask | L | 3-0 | |
| TT Cup (2023) | 07/12 06:15 | - | Kalle Kask v Aleksandr Dulov | L | 1-3 | |
| TT Cup (2023) | 03/17 10:15 | - | Kalle Kask v Yuto Kobayashi | W | 3-0 | |
| TT Cup (2023) | 03/17 09:15 | - | Kalle Kask v Johannes Kant | W | 3-0 | |
| TT Cup (2023) | 03/17 07:15 | - | Kalle Kask v Valdek Putkemaa | W | 3-0 | |
| TT Cup (2023) | 03/17 06:45 | - | Kalle Kask v Yuto Kobayashi | W | 3-2 | |
| TT Cup (2023) | 02/03 10:15 | - | Stanislav Kruti v Kalle Kask | L | 3-0 | |
| TT Cup (2023) | 02/03 08:45 | - | Johannes Kant v Kalle Kask | W | 0-3 | |
| TT Cup (2023) | 02/03 08:15 | - | Yuto Kobayashi v Kalle Kask | W | 2-3 | |
| TT Cup (2023) | 02/03 07:15 | - | Kalle Kask v Stanislav Kruti | L | 0-3 | |
| TT Cup (2023) | 01/27 09:45 | - | Valdek Putkemaa v Kalle Kask | L | 3-0 | |
| TT Cup (2023) | 01/27 08:45 | - | Kalle Kask v Elvis Libene | L | 0-3 | |
| TT Cup (2023) | 01/27 07:45 | - | Kalle Kask v Valdek Putkemaa | L | 0-3 | |
| TT Cup (2023) | 01/27 06:45 | - | Kalle Kask v Stanislav Kruti | L | 1-3 | |
| TT Cup (2022) | 12/19 13:15 | - | Kalle Kask v Johannes Kant | - | Cancelled | |
| TT Cup (2022) | 12/19 12:15 | - | Kalle Kask v Ermo Veelain | - | Cancelled | |
| TT Cup (2022) | 12/19 11:15 | - | Kalle Kask v Valdek Putkemaa | - | Cancelled | |
| TT Cup (2022) | 11/23 10:15 | - | Kalle Kask v Stanislav Kruti | L | 1-3 | |
| TT Cup (2022) | 11/23 08:15 | - | Kalle Kask v Johannes Kant | W | 3-2 | |
| TT Cup (2022) | 11/23 07:15 | - | Kalle Kask v Vootele Vaher | W | 3-2 | |
| TT Cup (2022) | 11/23 06:45 | - | Kalle Kask v Stanislav Kruti | W | 3-2 | |
| TT Cup (2022) | 07/20 09:15 | - | Kalle Kask v Johannes Kant | L | 2-3 | |
| TT Cup (2022) | 07/20 08:15 | - | Johannes Kant v Kalle Kask | W | 2-3 | |
| TT Cup (2022) | 07/20 07:45 | - | Kalle Kask v Urmas Roos | W | 3-1 | |
| TT Cup (2022) | 07/20 06:15 | - | Kalle Kask v Vootele Vaher | W | 3-2 | |
| TT Cup (2022) | 06/09 09:15 | - | Vootele Vaher v Kalle Kask | W | 0-3 | |
| TT Cup (2022) | 06/09 07:15 | - | Martin Pakk v Kalle Kask | W | 1-3 | |
| TT Cup (2022) | 06/09 06:15 | - | Valdek Putkemaa v Kalle Kask | W | 0-3 |