| TT Cup | 03/14 19:45 | - | Le Liu v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup | 03/14 18:45 | - | Mart Martin v Markus-Oliver Annuk | W | 2-3 | |
| TT Cup | 03/14 17:45 | - | Markus-Oliver Annuk v Markus Poru | W | 3-1 | |
| TT Cup | 03/14 16:15 | - | Le Liu v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup | 03/08 10:15 | - | Markus-Oliver Annuk v Mart Martin | W | 3-0 | |
| TT Cup | 03/08 08:45 | - | Markus-Oliver Annuk v Edvinas Tamashauskas | W | 3-2 | |
| TT Cup | 03/08 07:45 | - | Markus-Oliver Annuk v Mart Martin | W | 3-1 | |
| TT Cup | 03/08 06:45 | - | Markus-Oliver Annuk v Yevhenii Cherkashyn | W | 3-0 | |
| TT Cup | 03/06 19:30 | - | Mart Martin v Markus-Oliver Annuk | L | 3-0 | |
| TT Cup | 03/06 18:15 | - | Martin Mart v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup | 03/06 17:45 | - | Marko Mannik v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup | 03/06 16:45 | - | Markus-Oliver Annuk v Le Liu | L | 0-3 | |
| TT Cup | 02/10 09:50 | - | Sander Taaber v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup | 02/10 09:15 | - | Markus-Oliver Annuk v Dmitri Kuznetsov | L | 1-3 | |
| TT Cup | 02/10 07:45 | - | Maksim Sharofost v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup | 02/10 07:15 | - | Sander Taaber v Markus-Oliver Annuk | L | 3-0 | |
| TT Cup | 02/09 10:15 | - | Heiki Magi v Markus-Oliver Annuk | W | 2-3 | |
| TT Cup | 02/09 08:45 | - | Edvinas Tamashauskas v Markus-Oliver Annuk | W | 1-3 | |
| TT Cup | 02/09 08:15 | - | Heiki Magi v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup | 02/09 07:15 | - | Markus-Oliver Annuk v Mart Martin | W | 3-1 | |
| TT Cup | 02/06 19:25 | - | Sander Taaber v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup | 02/06 18:15 | - | Sander Taaber v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup | 02/06 17:45 | - | Varmo Onton v Markus-Oliver Annuk | L | 3-0 | |
| TT Cup | 02/06 16:45 | - | Markus-Oliver Annuk v Marko Mannik | L | 2-3 | |
| TT Cup | 12/29 09:45 | - | Markus-Oliver Annuk v Sergei Provodin | W | 3-0 | |
| TT Cup (2023) | 12/29 08:45 | - | Daljus Kregzde v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup (2023) | 12/29 08:15 | - | Heiki Magi v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup (2023) | 12/29 07:15 | - | Markus-Oliver Annuk v Sergei Provodin | W | 3-0 | |
| TT Cup (2023) | 12/21 09:50 | - | Markus-Oliver Annuk v Andres Lofitski | W | 3-2 | |
| TT Cup (2023) | 12/21 08:45 | - | Heiki Magi v Markus-Oliver Annuk | L | 3-0 |