Round: 26 Ground: Hardcourt outdoor
| ITF M15 Wellington | 2023/12/11 23:30 | Gillian Osmont v Sam Thompson | 3-6,2-6 |
| Davis Cup | 2023/07/29 04:30 | Hamid Reza Nadaf v Gillian Osmont | 6-2,6-2 |
| Challenger Noumea | 2023/01/01 00:00 | Gillian Osmont v Kaito Uesugi | 3-6,1-6 |
| ITF M15 Tauranga | 2022/12/18 23:10 | Blake Ellis v Gillian Osmont | 6-1,6-4 |
| ITF M15 Wellington | 2022/12/12 02:45 | Rhys Searant v Gillian Osmont | 6-3,6-0 |
| ITF M15 Sharm El Sheikh | 2022/11/27 12:30 | Sanhui Shin v Gillian Osmont | 6-3,6-2 |
| ITF M15 Sharm El Sheikh | 2022/11/20 08:00 | Gillian Osmont v Maks Lukman | 6-3,1-6,10-12 |
| ITF M15 Caloundra | 2022/07/25 00:00 | Gillian Osmont v Arjun Mehrotra | 3-6,1-6 |
| ITF M15 Wellington | 2023/12/15 23:20 | Matthew Dellavedova v Matt Kuhar | 2-6,6-2,6-1 |
| ITF M15 Wellington | 2023/12/14 21:00 | Jayden Court v Matt Kuhar | 4-6,4-6 |
| ITF M15 Wellington | 2023/12/13 22:35 | Corban Crowther v Matt Kuhar | 1-6,4-6 |
| ITF M15 Wellington | 2023/12/13 00:40 | Sam Thompson v Matt Kuhar | 2-6,2-6 |
| ITF M15 Wellington | 2023/12/10 23:15 | Matt Kuhar v Keegan Smith | 6-3,1-6,6-4 |
| ITF M15 Tallahassee | 2023/10/26 15:00 | James Connel v Matt Kuhar | 7-6,5-7,6-2 |
| ITF M15 Tallahassee | 2023/10/24 14:00 | Matt Kuhar v Huzaifa Abdul Rehman | 6-0,7-6 |
| ITF M15 Ithaca | 2023/10/05 16:35 | Alex Rybakov v Matt Kuhar | 6-4,7-5 |