Stadium: Court 2 Round: 54 Ground: Clay
| ITF W100 Charleston | 2023/04/17 18:10 | Alexandra Osborne v Olivia Tjandramulia | 2-6,4-6 |
| ITF W25 Gatineau | 2019/07/17 14:00 | Olivia Tjandramulia v Alexandra Osborne | 6-7,2-6 |
| ITF W60 Charlottesville | 2023/04/24 19:55 | Elysia Bolton v Olivia Tjandramulia | 6-1,6-2 |
| ITF W100 Charleston | 2023/04/18 15:40 | Renata Zarazua v Olivia Tjandramulia | 6-1,6-1 |
| ITF W100 Charleston | 2023/04/17 18:10 | Alexandra Osborne v Olivia Tjandramulia | 2-6,4-6 |
| ITF W60 Irapuato | 2023/02/15 19:55 | Marcela Zacarias v Olivia Tjandramulia | 7-5,7-5 |
| ITF W60 Irapuato | 2023/02/13 20:00 | Gabriela Ce v Olivia Tjandramulia | 6-0,7-5 |
| ITF W60 Irapuato | 2023/02/12 18:25 | Ximena N Hernandez v Olivia Tjandramulia | 1-6,1-6 |
| ITF W60 Orlando | 2023/02/07 14:50 | Renata Zarazua v Olivia Tjandramulia | 6-0,6-4 |
| ITF W60 Orlando | 2023/02/06 15:00 | Allura Zamarripa v Olivia Tjandramulia | 4-6,4-6 |
| 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 |
| ITF W60 Canberra Qual | 2023/03/18 23:00 | Alexandra Osborne v Jelena Cvijanovic | 6-1,6-7,6-3 |
| ITF W60 Canberra | 2023/03/11 22:50 | Alexandra Osborne v Elena Micic | 1-6,3-6 |
| ITF W25 Swan Hill | 2023/02/28 02:30 | Ya-Yi Yang v Alexandra Osborne | 1-6,6-2,6-3 |