Stadium: Court 2 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2023/05/15 12:30 | Linang Xiao v Winter Meagher | 7-5,6-1 |
| ITF M15 Monastir | 2023/05/14 12:00 | Adam Bojkovic v Winter Meagher | 2-6,4-6 |
| ITF M15 Monastir | 2023/05/07 10:30 | Mohamed Ali Abibsi v Winter Meagher | 6-3,6-7,10-8 |
| ITF M15 Monastir | 2023/05/01 12:30 | Yamato Sueoka v Winter Meagher | 6-1,6-3 |
| ITF M15 Monastir | 2023/05/01 08:30 | Winter Meagher v Hillel Rousseau | 6-0,6-2 |
| ITF M15 Monastir | 2023/04/30 11:30 | Darrshan Suresh v Winter Meagher | 3-6,3-6 |
| ITF M25 Canberra | 2023/03/19 23:00 | Corey Gaal v Winter Meagher | 6-4,6-4 |
| ITF M25 Canberra | 2023/03/19 01:30 | Winter Meagher v Nicholas Jovanovski | 7-5,6-1 |