Stadium: Court 2 Round: 54 Ground: Hardcourt outdoor
| ITF - W40 Porto | 2023/07/16 12:30 | Chelsea Fontenel v Alexandra Osborne | 7-6,5-7,6-2 |
| ITF W60 - Rome | 2023/07/10 12:05 | Alexandra Osborne v Julia Terziyska | 1-6,2-6 |
| ITF W25 - Perigueux | 2023/06/26 11:05 | Alexandra Osborne v Lucie Pawlak | 2-6,2-6 |
| ITF W100 - Ilkley | 2023/06/19 09:30 | Alexandra Osborne v Zhuoxuan Bai | 4-6,1-6 |
| ITF - W60 Naples | 2023/05/09 15:20 | Alexandra Osborne v Haley Giavara | 2-6,6-4,3-6 |
| ITF - W60 Naples | 2023/05/08 14:00 | Alexandra Osborne v Ena Koike | 6-2,7-6 |
| ITF - W100 Bonita Springs | 2023/05/01 19:20 | Olivia Tjandramulia v Alexandra Osborne | 7-5,6-4 |
| ITF W60 - Charlottesville | 2023/04/24 16:35 | Grace Min v Alexandra Osborne | 6-7,6-2,6-4 |
| UTR Pro - Florida - Dames | 2023/06/03 18:45 | Taly Licht v Annabelle Davis | 5-7,3-6 |
| UTR Pro - Florida - Dames | 2023/06/02 19:30 | Jennifer Jackson v Annabelle Davis | 4-6,3-6 |
| UTR Pro - Florida - Dames | 2023/06/01 16:30 | Kathryn Treiber v Annabelle Davis | 3-6,3-6 |
| UTR Pro - Florida - Dames | 2023/05/31 16:30 | Samantha Crawford v Annabelle Davis | 6-1,6-4 |
| UTR Pro - Florida - Dames | 2023/05/29 18:00 | Ichino Horikawa v Annabelle Davis | 6-1,6-3 |
| UTR Pro - Florida - Dames | 2023/01/07 17:30 | Annabelle Davis v Ekaterina Khayrutdinova | 2-6,2-6 |
| UTR Pro - Florida - Dames | 2023/01/06 18:00 | Akasha Urhobo v Annabelle Davis | 4-6,4-6 |
| UTR Pro - Florida - Dames | 2023/01/04 17:30 | Quinn Gleason v Annabelle Davis | 6-2,6-1 |