| TT Cup (2023) | 06/27 11:45 | - | Koit Karjus v Heldur Nermann | L | 3-2 | |
| TT Cup (2023) | 06/27 10:45 | - | Heldur Nermann v Eduard Pukkonen | L | 0-3 | |
| TT Cup (2023) | 05/30 13:45 | - | Yuto Kobayashi v Heldur Nermann | L | 3-0 | |
| TT Cup (2023) | 05/30 12:45 | - | Heino Laidmaa v Heldur Nermann | W | 1-3 | |
| TT Cup (2023) | 05/30 11:45 | - | Heldur Nermann v Johannes Kant | W | 3-1 | |
| TT Cup (2023) | 05/30 10:15 | - | Yuto Kobayashi v Heldur Nermann | L | 3-0 | |
| TT Cup (2023) | 04/22 09:15 | - | Dmitri Donskov v Heldur Nermann | L | 3-0 | |
| TT Cup (2023) | 04/22 07:45 | - | Heldur Nermann v Martin Printsmann | W | 3-1 | |
| TT Cup (2023) | 04/22 06:45 | - | Heldur Nermann v Ular Nurmits | W | 3-2 | |
| TT Cup (2023) | 04/22 05:45 | - | Heldur Nermann v Dmitri Donskov | L | 0-3 | |
| TT Cup (2023) | 03/24 14:15 | - | Heldur Nermann v Mark Jarovoi | L | 0-3 | |
| TT Cup (2023) | 03/24 13:15 | - | Heldur Nermann v Yuto Kobayashi | L | 0-3 | |
| TT Cup (2023) | 03/24 12:15 | - | Heldur Nermann v Raul Pirson | L | 1-3 | |
| TT Cup (2023) | 03/24 11:15 | - | Heldur Nermann v Mark Jarovoi | W | 3-1 | |
| TT Cup (2023) | 03/15 09:45 | - | Ermo Veelain v Heldur Nermann | W | 2-3 | |
| TT Cup (2023) | 03/15 08:45 | - | Heldur Nermann v Ermo Veelain | L | 0-3 | |
| TT Cup (2023) | 03/15 07:45 | - | Heldur Nermann v Oliver Ollman | L | 0-3 | |
| TT Cup (2023) | 03/15 06:45 | - | Heldur Nermann v Raul Pirson | L | 1-3 | |
| TT Cup (2023) | 03/12 09:45 | - | Heldur Nermann v Ular Nurmits | W | 3-1 | |
| TT Cup (2023) | 03/12 08:45 | - | Heldur Nermann v Jevgeni Sikorski | L | 2-3 | |
| TT Cup (2023) | 03/12 07:45 | - | Heldur Nermann v Ular Nurmits | W | 3-0 | |
| TT Cup (2023) | 03/12 06:45 | - | Heldur Nermann v Toivo Tuisk | L | 0-3 | |
| TT Cup (2023) | 02/21 14:15 | - | Heldur Nermann v Andrei Romanov | W | 3-1 | |
| TT Cup (2023) | 02/21 13:45 | - | Heldur Nermann v Madis Vaarpu | L | 0-3 | |
| TT Cup (2023) | 02/21 12:15 | - | Andrei Romanov v Heldur Nermann | W | 0-3 | |
| TT Cup (2023) | 02/21 11:45 | - | Ermo Veelain v Heldur Nermann | L | 3-0 | |
| TT Cup (2023) | 02/01 09:45 | - | Heldur Nermann v Andi Maasalu | W | 3-0 | |
| TT Cup (2023) | 02/01 09:15 | - | Raul Pirson v Heldur Nermann | L | 3-2 | |
| TT Cup (2023) | 02/01 08:15 | - | Heldur Nermann v Andi Maasalu | W | 3-0 | |
| TT Cup (2023) | 02/01 06:45 | - | Mart Ojamaa v Heldur Nermann | L | 3-0 |