Stadium: Court 7 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2023/07/18 10:20 | Kody Pearson v Matthew William Donald | 6-1,6-2 |
| ITF M15 Wroclaw | 2023/06/29 08:00 | Matthew William Donald v Sergey Fomin | 2-6,6-4,2-6 |
| ITF M15 Wroclaw | 2023/06/28 09:40 | Fryderyk Lechno-Wasiutynski v Matthew William Donald | 6-4,3-6,4-6 |
| ITF M15 Store | 2023/06/21 11:00 | Lorenzo Bocchi v Matthew William Donald | 6-4,6-4 |
| ITF M25 Jablonec Nad Nisou | 2023/05/31 09:30 | Matthew William Donald v Michael Vrbensky | 6-7,1-6 |
| ITF M25 Jablonec Nad Nisou | 2023/05/30 09:30 | Matthew William Donald v Lukas Janousek | 6-0,6-2 |
| ITF M25 Jablonec Nad Nisou | 2023/05/28 10:30 | Matthew William Donald v Julian Peter | 6-1,6-0 |
| ITF M25 Most | 2023/05/24 09:35 | Mats Moraing v Matthew William Donald | 6-2,6-0 |
| ITF M15 Monastir | 2023/07/19 09:30 | Cyril Vandermeersch v Gabriele Bosio | 6-2,6-2 |
| ITF M15 Monastir | 2023/07/16 08:00 | Gabriele Bosio v Sandro Cottino | 6-3,6-4 |
| ITF M15 Monastir | 2023/07/13 08:00 | Yassine Dlimi v Gabriele Bosio | 6-2,6-1 |
| ITF M15 Monastir | 2023/07/12 08:00 | Tuncay Duran v Gabriele Bosio | 6-7,7-5,3-6 |
| ITF M15 Monastir | 2023/07/07 11:05 | Coleman Wong v Gabriele Bosio | 6-3,6-3 |
| ITF M15 Monastir | 2023/07/06 10:40 | Gabriele Bosio v Boris Butulija | 2-6,6-1,6-2 |
| ITF M15 Monastir | 2023/07/05 10:05 | Gabriele Bosio v Stefan Vujic | 6-3,6-0 |
| Challenger Modena | 2023/06/25 08:00 | Gabriele Bosio v Lucas Gerch | 4-6,4-6 |