Stadium: Court 16 Round: 14 Ground: Hardcourt outdoor
| Challenger Alicante | 2022/10/05 09:00 | Dimitar Kuzmanov v Billy Harris | 6-4,6-4 |
| Challenger Saint-Tropez | 2023/09/18 11:30 | Mathias Bourgue v Billy Harris | 7-6,6-7,2-6 |
| Challenger Saint-Tropez | 2023/09/17 09:40 | Tom Paris v Billy Harris | 4-6,4-6 |
| Challenger Cassis | 2023/09/08 08:30 | Billy Harris v Liam Broady | 4-6,3-6 |
| Challenger Cassis | 2023/09/06 08:30 | Elmer Moller v Billy Harris | 1-6,5-7 |
| Challenger Cassis | 2023/09/05 08:00 | Mark Lajal v Billy Harris | 3-6,6-7 |
| Challenger Augsburg | 2023/08/22 09:20 | Gianmarco Ferrari v Billy Harris | 6-7,6-1,6-4 |
| Challenger Winnipeg | 2023/08/17 16:00 | Billy Harris v Liam Broady | 6-7,4-6 |
| Challenger Winnipeg | 2023/08/16 17:00 | Luca Nardi v Billy Harris | 4-6,7-5,5-7 |
| Davis Cup | 2023/09/17 09:30 | Dimitar Kuzmanov v Alexander Bublik | 4-6,6-7 |
| Davis Cup | 2023/09/16 09:30 | Dimitar Kuzmanov v Timofey Skatov | 6-3,4-6,3-6 |
| Challenger Tulln | 2023/09/08 11:15 | Dimitar Kuzmanov v Vit Kopriva | 1-6,1-6 |
| Challenger Tulln | 2023/09/06 09:35 | Dalibor Svrcina v Dimitar Kuzmanov | 6-2,4-6,2-6 |
| Challenger Tulln | 2023/09/05 10:20 | Dimitar Kuzmanov v Dennis Novak | 6-7,6-2,7-5 |
| Challenger Como | 2023/09/01 13:00 | Benoit Paire v Dimitar Kuzmanov | 4-6,6-4,6-3 |
| Challenger Como | 2023/08/30 08:00 | Dimitar Kuzmanov v Miljan Zekic | 6-2,6-3 |
| US Open | 2023/08/23 19:50 | Thiago Seyboth Wild v Dimitar Kuzmanov | 7-6,6-7,6-4 |