Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| WTA Chicago | 2021/08/16 16:00 | Vitalia Diatchenko v Dalayna Hewitt | 7-6,6-3 |
| ITF - Monastir W15 | 2021/07/25 08:30 | Dalayna Hewitt v Ayumi Koshiishi | 6-4,6-4 |
| ITF - Monastir W15 | 2021/07/24 08:20 | Dalayna Hewitt v Solymar Colling | 7-5,6-0 |
| ITF - Monastir W15 | 2021/07/23 10:35 | Dalayna Hewitt v Katja Wiersholm | 6-4,6-2 |
| ITF - Monastir W15 | 2021/07/22 08:30 | Anastasia E Nefedova v Dalayna Hewitt | 4-6,2-6 |
| ITF - Monastir W15 | 2021/07/21 13:30 | Valeria Bhunu v Dalayna Hewitt | 7-5,5-7,3-6 |
| ITF - Monastir W15 | 2021/07/15 08:25 | Dalayna Hewitt v Maria Kozyreva | 6-1,4-6,3-6 |
| ITF - Monastir W15 | 2021/07/13 11:00 | Jade Bornay v Dalayna Hewitt | 2-6,6-4,3-6 |
| ITF - Monastir W15 | 2021/08/31 09:00 | Margaux Komano v Milana Zhabrailova | 1-6,2-6 |
| ITF - Monastir W15 | 2021/08/30 12:00 | Alejandra Gutierrez v Milana Zhabrailova | 0-6,3-6 |
| ITF - Monastir W15 | 2021/08/25 16:05 | Milana Zhabrailova v Himeno Sakatsume | 5-7,1-6 |
| ITF - Monastir W15 | 2021/08/24 08:30 | Brittany Collens v Milana Zhabrailova | 3-6,1-6 |
| ITF - Monastir W15 | 2021/08/23 14:30 | Milana Zhabrailova v Giuliana Bestetti | 6-1,6-0 |
| ITF - Monastir W15 | 2021/08/22 14:30 | Milana Zhabrailova v Sharrmadaa Baluu | 6-1,6-3 |
| ITF - Monastir W15 | 2021/08/17 08:30 | Lea Magun v Milana Zhabrailova | 6-1,6-4 |
| ITF - Monastir W15 | 2021/08/16 16:00 | Milana Zhabrailova v Margaux Komano | 4-6,6-3,10-4 |