Stadium: Court 3 Round: 54 Ground: Clay
| ITF M15 Naples | 2021/10/04 14:00 | Benjamin Niv v Jake Krug | 4-6,5-7 |
| UTR Pro Tennis Series Dallas | 2021/08/03 17:30 | Jake Krug v Ryan Ybarra | 6-2,6-7,5-3 |
| UTR Pro Tennis Series Dallas | 2021/08/02 16:30 | Jake Krug v Matt Kuhar | 2-6,0-5 |
| UTR Pro Tennis Series Atlanta | 2021/07/08 14:30 | Alan Sau Franco v Jake Krug | 6-4,5-2 |
| UTR Pro Tennis Series Atlanta | 2021/07/07 13:00 | Maxwell Benson v Jake Krug | 6-4,6-1 |
| UTR Pro Tennis Series Atlanta | 2021/07/06 12:00 | Samuel Rubell v Jake Krug | 2-6,3-5 |
| UTR Pro Tennis Series Atlanta | 2021/07/05 16:30 | Gonzalo Villanueva v Jake Krug | 6-4,5-4 |
| UTR Pro Tennis Series Atlanta | 2021/07/04 13:30 | Jake Krug v Harvey Maughan | 6-2,1-0 |
| ITF M15 Naples | 2021/10/04 14:00 | Parth Aggarwal v Nikolay Sysoev | 2-6,5-7 |
| UTR Pro Tennis Series Florida | 2021/09/19 15:30 | Nikolay Sysoev v Timothy Phung | 7-5,1-6,5-3 |
| UTR Pro Tennis Series Florida | 2021/09/18 18:30 | Noureldin Adam v Nikolay Sysoev | 3-6,5-6 |
| UTR Pro Tennis Series Florida | 2021/09/16 19:30 | Nikolay Sysoev v Antonio M-Hidalgo | 6-3,7-5 |
| UTR Pro Tennis Series Florida | 2021/09/15 12:00 | Nikolay Sysoev v Roman Postolka | 2-6,2-6 |
| UTR Pro Tennis Series Florida | 2021/09/14 13:30 | Nikolay Sysoev v Michal Schmid | 6-7,2-5 |
| UTR Pro Tennis Series Florida | 2021/09/13 12:00 | Nikolay Sysoev v Omar Maldonado | 7-6,6-4 |
| ITF M15 Monastir | 2021/08/01 09:00 | Drew Baird v Nikolay Sysoev | 6-1,6-2 |