Stadium: Center court Round: 26 Ground: Hardcourt outdoor
| ITF M25 Johannesburg | 2021/09/21 10:25 | Francesco Vilardo v Khololwam Montsi | 4-6,5-7 |
| ITF M25 Johannesburg | 2021/09/14 11:30 | Joshua Howard-Tripp v Khololwam Montsi | 4-6,2-6 |
| ITF M15 Monastir | 2021/08/05 08:50 | Mattia Bellucci v Khololwam Montsi | 6-2,6-2 |
| ITF M15 Monastir | 2021/08/04 16:45 | Khololwam Montsi v Santiago Rodriguez Taverna | 7-5,7-5 |
| ITF M15 Monastir | 2021/07/31 07:30 | Luca Potenza v Khololwam Montsi | 7-5,6-1 |
| ITF M15 Monastir | 2021/07/30 07:25 | Khololwam Montsi v Matias Franco Descotte | 7-6,6-1 |
| ITF M15 Monastir | 2021/07/29 09:50 | Khololwam Montsi v Joshua Sheehy | 7-5,6-4 |
| ITF M15 Monastir | 2021/07/20 10:25 | Erik Crepaldi v Khololwam Montsi | 6-4,6-0 |
| ITF M25 Johannesburg | 2021/09/22 08:35 | Markos Kalovelonis v Makoto Ochi | 6-4,6-4 |
| ITF M25 Lesa | 2021/08/25 10:45 | Andrea Basso v Markos Kalovelonis | 6-3,6-2 |
| UTR Pro Tennis Series Barcelona | 2021/08/14 08:40 | Pablo Carretero v Markos Kalovelonis | 6-7,1-0 |
| UTR Pro Tennis Series Barcelona | 2021/08/12 13:00 | Markos Kalovelonis v Olexiy Kolisnyk | 4-6,4-6 |
| UTR Pro Tennis Series Barcelona | 2021/08/11 07:00 | Markos Kalovelonis v Xavier Gabarro | 6-3,6-0 |
| UTR Pro Tennis Series Barcelona | 2021/08/10 10:00 | Markos Kalovelonis v Andrey Chepelev | 6-7,6-2,3-5 |
| UTR Pro Tennis Series Barcelona | 2021/08/09 13:45 | Markos Kalovelonis v Jaume Pla Malfeito | 6-3,5-3 |
| ITF M25 Telavi | 2021/07/30 06:00 | Marco De Rossi v Markos Kalovelonis | 6-3,6-3 |