Stadium: Centre Court Round: 54 Ground: Grass
| French Open Women | 2023/05/24 16:10 | Yanina Wickmayer v Olga Danilovic | 3-6,2-6 |
| French Open Women | 2023/05/23 16:45 | Ana Konjuh v Yanina Wickmayer | 3-6,0-6 |
| ITF W100 Trnava | 2023/05/14 09:30 | Greet Minnen v Yanina Wickmayer | 0-6,3-6 |
| ITF W100 Trnava | 2023/05/13 10:45 | Chloe Paquet v Yanina Wickmayer | 2-6,6-4,4-6 |
| ITF W100 Trnava | 2023/05/10 13:35 | Yanina Wickmayer v Conny Perrin | 6-1,5-7,6-4 |
| ITF W100 Wiesbaden | 2023/05/04 12:40 | Yanina Wickmayer v Simona Waltert | 6-1,3-6,6-7 |
| ITF W100 Wiesbaden | 2023/05/03 09:00 | Ksenia Laskutova v Yanina Wickmayer | 4-6,2-6 |
| Billie Jean King Cup | 2023/04/14 23:00 | Leylah Annie Fernandez v Yanina Wickmayer | 6-0,6-3 |
| 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 |
| ITF W100 Charleston | 2023/04/17 18:10 | Alexandra Osborne v Olivia Tjandramulia | 2-6,4-6 |
| ITF W25 Jackson | 2023/04/04 15:00 | Alexandra Osborne v Ena Koike | 7-6,0-6,6-10 |
| ITF W60 Canberra | 2023/03/21 00:00 | Yuki Naito v Alexandra Osborne | 2-6,6-0,6-4 |
| ITF W60 Canberra | 2023/03/19 23:00 | Alexandra Osborne v Erina Hayashi | 6-2,6-3 |