Stadium: Court 18 Round: 54 Ground: Clay
| ITF M25 Pretoria | 2021/10/02 11:30 | Montsi, Khololwam v Rio Noguchi | 5-7,2-6 |
| ITF M25 Pretoria | 2021/10/01 13:35 | Prechtel, Sebastian v Montsi, Khololwam | 2-6,3-6 |
| ITF M25 Pretoria | 2021/09/29 10:45 | Montsi, Khololwam v Goldsteiner, Peter | 6-4,6-3 |
| ITF M25 Johannesburg | 2021/09/24 07:55 | Alastair Gray v Montsi, Khololwam | 6-2,6-4 |
| ITF M25 Johannesburg | 2021/09/23 08:00 | Montsi, Khololwam v Kalovelonis, Markos | 6-1,6-3 |
| ITF M25 Johannesburg | 2021/09/21 10:25 | Vilardo, Francesco v Montsi, Khololwam | 4-6,5-7 |
| ITF M25 Johannesburg | 2021/09/14 11:30 | Howard-Tripp, Joshua v Montsi, Khololwam | 4-6,2-6 |
| ITF - M15 Monastir | 2021/08/05 08:50 | Mattia Bellucci v Montsi, Khololwam | 6-2,6-2 |
| ITF - M25 Santo Domingo | 2021/12/05 14:00 | Juan Luis Yanine v Foster-Estwick, Matthew | 2-6,6-4,10-6 |
| ITF - M15 Santo Domingo | 2021/12/01 18:05 | Foster-Estwick, Matthew v Musialek, Alexis | 0-6,2-6 |
| ITF - M25 Santo Domingo | 2021/11/30 13:00 | Matt Kuhar v Foster-Estwick, Matthew | 6-3,6-2 |
| ITF M15 Guatemala | 2021/11/22 16:00 | Foster-Estwick, Matthew v Jeffrey Hsu | 6-4,4-6,4-10 |
| ITF M15 East Lansing | 2021/11/15 18:00 | Adit Sinha v Foster-Estwick, Matthew | 6-1,6-1 |
| UTR Pro Tennis Series Miami | 2021/11/07 13:00 | Foster-Estwick, Matthew v Tyler Bowers | 1-6,0-4 |
| UTR Pro Tennis Series Miami | 2021/11/04 19:30 | Elio Jose Ribeiro Lago v Foster-Estwick, Matthew | 7-5,5-2 |
| UTR Pro Tennis Series Miami | 2021/11/04 15:30 | Leote Prata, Martim v Foster-Estwick, Matthew | 6-1,6-4 |