| TT Cup (2023) | 12/21 08:15 | - | Daljus Kregzde v Markus-Oliver Annuk | L | 3-0 | |
| TT Cup (2023) | 12/21 07:15 | - | Markus-Oliver Annuk v Andres Lofitski | W | 3-0 | |
| TT Cup (2023) | 12/11 14:20 | - | Sergei Provodin v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup (2023) | 12/11 13:15 | - | Markus-Oliver Annuk v Sergei Provodin | L | 2-3 | |
| TT Cup (2023) | 12/11 12:15 | - | Markus-Oliver Annuk v Indrek Perv | L | 0-3 | |
| TT Cup (2023) | 12/11 11:15 | - | Markus-Oliver Annuk v Heiki Magi | L | 1-3 | |
| TT Cup (2023) | 10/08 13:20 | - | Daljus Kregzde v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup (2023) | 10/08 12:45 | - | Markus-Oliver Annuk v Heiki Magi | L | 1-3 | |
| TT Cup (2023) | 10/08 11:15 | - | Daljus Kregzde v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup (2023) | 10/08 10:45 | - | Erik Trofimov v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup (2023) | 09/12 18:15 | - | Le Liu v Markus-Oliver Annuk | W | 1-3 | |
| TT Cup (2023) | 09/12 17:45 | - | Erik Trofimov v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup (2023) | 09/12 16:45 | - | Markus-Oliver Annuk v Le Liu | L | 0-3 | |
| TT Cup (2023) | 09/12 15:15 | - | Sander Taaber v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup (2023) | 09/04 18:45 | - | Markus-Oliver Annuk v Indrek Perv | W | 3-2 | |
| TT Cup (2023) | 09/04 17:45 | - | Markus-Oliver Annuk v Marko Mannik | W | 3-2 | |
| TT Cup (2023) | 09/04 16:15 | - | Indrek Perv v Markus-Oliver Annuk | W | 1-3 | |
| TT Cup (2023) | 09/04 15:45 | - | Le Liu v Markus-Oliver Annuk | W | 2-3 | |
| TT Cup (2023) | 08/28 08:45 | - | Philip Kharchenko v Markus-Oliver Annuk | L | 3-0 | |
| TT Cup (2023) | 08/28 07:45 | - | Daljus Kregzde v Markus-Oliver Annuk | L | 3-0 | |
| TT Cup (2023) | 08/28 07:15 | - | Philip Kharchenko v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup (2023) | 08/28 06:15 | - | Markus-Oliver Annuk v Dmitri Kuznetsov | L | 0-3 | |
| TT Cup (2023) | 08/24 18:15 | - | Le Liu v Markus-Oliver Annuk | W | 0-3 | |
| TT Cup (2023) | 08/24 17:45 | - | Le Liu v Markus-Oliver Annuk | L | 3-2 | |
| TT Cup (2023) | 08/24 16:45 | - | Markus-Oliver Annuk v Dmitri Krasnov | L | 0-3 | |
| TT Cup (2023) | 08/24 15:15 | - | Sander Taaber v Markus-Oliver Annuk | L | 3-1 | |
| TT Cup (2023) | 08/21 08:45 | - | Markus-Oliver Annuk v Indrek Perv | W | 3-0 | |
| TT Cup (2023) | 08/21 08:15 | - | Indrek Perv v Markus-Oliver Annuk | W | 1-3 | |
| TT Cup (2023) | 08/21 07:15 | - | Markus-Oliver Annuk v Philip Kharchenko | L | 1-3 | |
| TT Cup (2023) | 08/21 05:45 | - | Dmitri Kuznetsov v Markus-Oliver Annuk | L | 3-0 |