Stadium: Court 5 Round: 54 Ground: Clay
| ITF W60 Charleston | 2021/06/23 13:30 | Maria Mateas v Katerina Stewart | 6-4,0-6,7-6 |
| ITF W25 Pelham | 2021/05/19 16:00 | Katerina Stewart v Fernanda Contreras Gomez | 1-6,2-6 |
| ITF W100 Bonita Springs | 2021/05/10 18:55 | Katerina Stewart v Ulrikke Eikeri | 5-7,5-7 |
| ITF W25 Naples | 2021/05/07 13:30 | Irina Fetecau v Katerina Stewart | 6-2,1-6,6-1 |
| ITF W25 Naples | 2021/05/06 13:00 | Katerina Stewart v Kayla Day | 3-6,6-2,6-2 |
| ITF W25 Naples | 2021/05/05 20:55 | Katerina Stewart v Anna Siskova | 1-6,6-2,6-3 |
| ITF W60 Charlottesville | 2021/04/26 18:55 | Kayla Day v Katerina Stewart | 6-3,6-3 |
| WTA Charleston | 2021/04/03 14:00 | Katerina Stewart v Grace Min | 2-6,1-6 |
| ITF W25 Haag | 2021/06/27 08:00 | Rebeca Pereira v Alexandra Osborne | 7-6,6-1 |
| ITF W15 Alkmaar | 2021/06/23 09:00 | Alexandra Osborne v Quirine Lemoine | 3-6,0-6 |
| ITF W25 Madrid | 2021/06/16 08:00 | Na-Lae Han v Alexandra Osborne | 6-4,6-0 |
| ITF W25 Madrid | 2021/06/15 07:00 | Ashlyn Krueger v Alexandra Osborne | 6-1,4-6,5-10 |
| ITF W25 Madrid | 2021/06/14 09:30 | Elizabeth Jurna v Alexandra Osborne | 1-6,4-6 |
| ITF W25 Madrid | 2021/06/13 10:00 | Alexandra Osborne v Kamilla Bartone | 6-0,6-2 |
| ITF W25 Madrid | 2021/06/07 07:15 | Judith P Saavedra v Alexandra Osborne | 7-6,6-7,10-6 |
| ITF W25 Madrid | 2021/06/06 12:00 | Daria Krasnova v Alexandra Osborne | 4-6,7-6,8-10 |