Stadium: Estadio Puerto Vallarta Round: 14 Ground: Hardcourt outdoor
| Challenger Champaign | 2021/11/19 18:25 | Kirkov, Vasil v Wolf, Jeffrey John | 3-6,2-6 |
| Challenger Champaign | 2021/11/17 16:00 | Kirkov, Vasil v Nick Chappell | 6-2,6-3 |
| Challenger Champaign | 2021/11/15 21:05 | Gunneswaran, Prajnesh v Kirkov, Vasil | 5-7,1-6 |
| ITF M15 Ithaca | 2021/11/06 13:55 | Johnson, Luke v Kirkov, Vasil | 6-1,6-1 |
| ITF M15 Ithaca | 2021/11/05 13:50 | Evan Bynoe v Kirkov, Vasil | 1-6,1-6 |
| ITF M15 Ithaca | 2021/11/04 16:45 | Colin Sinclair v Kirkov, Vasil | 3-6,4-6 |
| ITF M15 Ithaca | 2021/11/03 18:35 | Mcnally, John v Kirkov, Vasil | 7-6,2-6,1-6 |
| ITF M15 Tallahassee | 2021/10/31 14:00 | Johannes Ingildsen v Kirkov, Vasil | 6-4,1-6,2-6 |
| ITF M15 Cancun | 2021/10/18 15:00 | Aramburu Contreras, Ivar Jose v Juan Sebastian Osorio | 3-6,3-6 |
| ITF M15 Cancun | 2021/10/11 18:00 | Embry, Patricio v Aramburu Contreras, Ivar Jose | 4-6,6-4,10-6 |
| ITF M15 Cancun | 2021/10/11 14:00 | Reyna, Ricardo v Aramburu Contreras, Ivar Jose | 2-6,0-6 |
| ITF M15 Cancun | 2021/10/03 19:45 | Gomez, Mateo v Aramburu Contreras, Ivar Jose | 6-2,6-4 |
| ITF M15 Cancun | 2021/09/28 17:00 | Aramburu Contreras, Ivar Jose v Spec, Matic | 5-7,3-6 |
| ITF M15 Cancun | 2021/09/23 17:05 | Luis Britto v Aramburu Contreras, Ivar Jose | 6-2,7-6 |
| ITF M15 Cancun | 2021/09/21 14:00 | Martinez, Esdras v Aramburu Contreras, Ivar Jose | 1-6,1-6 |
| UTR Pro Tennis Series Cancun | 2021/04/03 13:00 | Aramburu Contreras, Ivar Jose v Zachery Foster | 5-7,6-3,4-5 |