Stadium: Court 2 Round: 54 Ground: Clay
| UTR Pro Tennis Series Copenhagen | 2021/06/20 11:00 | Jesper Klov Nilsson v Gustav Theilgaard | 3-6,0-3 |
| UTR Pro Tennis Series Copenhagen | 2021/06/19 11:30 | Gustav Theilgaard v Hugo Pierre | 6-4,7-5 |
| UTR Pro Tennis Series Copenhagen | 2021/06/18 08:00 | Sebastian Grundtvig Jorgensen v Gustav Theilgaard | 6-4,6-2 |
| UTR Pro Tennis Series Copenhagen | 2021/06/17 11:00 | Henrik Atlevi v Gustav Theilgaard | 5-7,2-6 |
| UTR Pro Tennis Series Copenhagen | 2021/06/15 08:22 | Maxim Landa v Gustav Theilgaard | 7-5,6-4 |
| UTR Pro Zadar | 2023/03/29 07:30 | Ivan Sergeyev v Duje Ajdukovic | 1-6,0-1 |
| UTR Pro Zadar | 2023/03/28 07:30 | Ivan Sergeyev v Oleg Prihodko | 6-4,3-6,0-6 |
| UTR Pro Zadar | 2023/03/27 06:45 | Andre Biro v Ivan Sergeyev | 2-6,6-3,6-0 |
| ITF M25 Palmanova | 2023/03/14 09:50 | Miguel Damas v Ivan Sergeyev | 6-1,6-3 |
| ITF M25 Palmanova | 2023/03/13 08:00 | Jiri Cizek v Ivan Sergeyev | 0-6,2-6 |
| ITF M25 Palmanova | 2023/03/12 12:00 | Joan Nadal Vives v Ivan Sergeyev | 3-6,4-6 |
| ITF M25 Antalya | 2023/02/05 07:00 | Rrezart Cungu v Ivan Sergeyev | 6-3,6-2 |
| ITF M15 Antalya | 2023/01/25 08:30 | Ivan Sergeyev v Nikola Puntaric | 6-2,6-0 |