Stadium: Court 2 Round: 24 Ground: Grass
| WTA Acapulco | 2020/02/23 22:00 | Giulia Gatto Monticone v Caroline Dolehide | 1-6,6-7 |
| French Open - Kobiety | 2021/05/25 17:05 | Tsvetana Pironkova v Caroline Dolehide | 6-7,6-2,6-4 |
| ITF - Bonita Springs W100 | 2021/05/12 15:35 | Francesca Di Lorenzo v Caroline Dolehide | 6-2,6-7,7-6 |
| ITF - Charleston W100 | 2021/05/05 16:55 | Caroline Dolehide v Aldila Sutjiadi | 1-6,6-2,4-6 |
| WTA Charleston Kwalifikacje | 2021/04/10 16:15 | Grace Min v Caroline Dolehide | 7-6,2-6,7-5 |
| WTA Charleston | 2021/04/06 17:25 | Caroline Dolehide v Hailey Baptiste | 3-6,3-6 |
| WTA Charleston | 2021/04/04 16:35 | Caroline Dolehide v Storm Hunter | 6-2,4-6,6-7 |
| WTA Charleston | 2021/04/03 15:40 | Caroline Dolehide v Mirjam Bjorklund | 6-4,6-3 |
| WTA Miami | 2021/03/22 21:40 | Timea Babos v Caroline Dolehide | 4-6,6-2,6-2 |
| French Open - Kobiety | 2021/05/25 16:00 | Kurumi Nara v Giulia Gatto Monticone | 6-4,6-2 |
| WTA Parma | 2021/05/18 15:05 | Giulia Gatto Monticone v Ludmilla Samsonova | 2-6,2-6 |
| WTA Rzym | 2021/05/08 12:15 | Alize Cornet v Giulia Gatto Monticone | 7-6,6-7,6-4 |
| WTA Bogota | 2021/04/08 15:00 | Tamara Zidansek v Giulia Gatto Monticone | 6-2,6-3 |
| WTA Bogota | 2021/04/06 15:00 | Astra Sharma v Giulia Gatto Monticone | 6-4,5-7,1-6 |
| WTA Bogota | 2021/04/04 20:10 | Giulia Gatto Monticone v Marie Benoit | 4-6,7-5,6-3 |
| WTA Bogota | 2021/04/03 19:30 | Giulia Gatto Monticone v Kelly L Vargas Gonzalez | 6-3,6-0 |
| ITF - Buenos Aires W25 | 2021/03/27 14:30 | Giulia Gatto Monticone v Carolina Alves | 2-6,1-6 |