Stadium: Court 5 Round: 62 Ground: Clay
| ITF M15 - Antalya | 2021/10/10 07:00 | Leyton Rivera v Mark Havlicek | 2-6,2-6 |
| ITF M15 Káhira | 2021/09/19 10:30 | Karan Singh v Leyton Rivera | 6-2,6-3 |
| ITF M15 Káhira | 2021/09/12 07:00 | Nitin Kumar Sinha v Leyton Rivera | 7-5,6-2 |
| ITF M15 Žilina | 2021/08/31 07:30 | Paul Valsecchi v Leyton Rivera | 6-3,6-4 |
| ITF M15 Žilina | 2021/08/30 07:30 | Jan Jermar v Leyton Rivera | 6-7,3-6 |
| ITF M15 Bratislava | 2021/08/23 09:00 | Janos Fekete v Leyton Rivera | 6-2,7-5 |
| ITF M15 Bratislava | 2021/08/17 08:00 | Leyton Rivera v Tomas Lanik | 6-7,2-6 |
| ITF M15 Frederiksberg | 2021/08/04 09:25 | Ryan Nijboer v Leyton Rivera | 6-4,6-2 |
| ITF M15 - Antalya | 2021/10/20 11:30 | Kalin Ivanovski v Billy Harris | 1-6,2-6 |
| ITF M25 Skopje | 2021/09/28 11:30 | Kalin Ivanovski v Clement Tabur | 5-7,3-6 |
| Davis Cup | 2021/06/24 08:00 | Kalin Ivanovski v Stefano Galvani | 6-3,6-3 |
| Davis Cup | 2021/06/23 08:00 | Kalin Ivanovski v Damien Gelabert | 6-2,6-2 |
| Davis Cup | 2021/06/22 08:00 | Kalin Ivanovski v Granit Bajraliu | 6-0,6-0 |
| ITF M15 Skopje | 2021/06/10 08:35 | Kalin Ivanovski v Obrad Markovski | 6-3,4-6,4-6 |
| ITF M15 Skopje | 2021/06/02 08:00 | Kalin Ivanovski v Alex Rybakov | 2-6,2-6 |
| ITF M15 Šibenik | 2021/05/19 12:30 | Rimpei Kawakami v Kalin Ivanovski | 6-0,6-2 |