Stadium: Court 2 Round: 45 Ground: Clay
| ITF Women Setubal Qual | 2018/07/07 15:30 | Olga Helmi v Sashi Kempster | 6-3,6-1 |
| ITF - W25 Porto | 2021/06/25 09:30 | Arianne Hartono v Olga Helmi | 6-0,4-6,6-2 |
| ITF - W25 Porto | 2021/06/24 12:35 | Olga Helmi v Yuriko Lily Miyazaki | 6-4,6-3 |
| ITF - W25 Porto | 2021/06/23 09:30 | Olga Helmi v Risa Ushijima | 6-0,6-1 |
| ITF - W25 Porto | 2021/06/22 10:25 | Melanie Stokke v Olga Helmi | 3-6,1-6 |
| ITF - W25 Porto | 2021/06/21 18:00 | Olga Parres Azcoitia v Olga Helmi | 0-6,5-7 |
| ITF - W25 Porto | 2021/06/20 12:00 | Barbara Balancho v Olga Helmi | 0-6,0-6 |
| ITF - W15 Monastir | 2021/05/23 08:30 | Ayumi Koshiishi v Olga Helmi | 3-6,2-6 |
| ITF - W15 Monastir | 2021/05/22 08:30 | Olga Helmi v Nadine Keller | 6-2,6-2 |
| ITF - W25 Porto | 2021/06/20 12:00 | Nina Ugrelidze v Sashi Kempster | 7-6,6-3 |
| ITF - W25 Figueira Da Foz | 2021/06/14 09:30 | Freya Christie v Sashi Kempster | 6-1,6-1 |
| ITF - W25 Figueira Da Foz | 2021/06/13 09:30 | Alexandra Silva v Sashi Kempster | 1-6,1-6 |
| ITF - W25 Montemor-O-Novo | 2021/06/07 09:00 | Hiroko Kuwata v Sashi Kempster | 6-3,6-3 |
| ITF - W25 Montemor-O-Novo | 2021/06/06 10:30 | Milla Sequeira v Sashi Kempster | 1-6,0-6 |
| ITF - W25 Oeiras | 2021/04/25 10:00 | Sarah Beth Grey v Sashi Kempster | 7-6,6-3 |
| ITF - W25 Oeiras | 2021/04/18 12:00 | Emily Webley-Smith v Sashi Kempster | 6-2,6-0 |
| ITF - W60 Oeiras | 2021/04/11 09:55 | Sashi Kempster v Olga Saez Larra | 1-6,2-6 |