Stadium: Court 1N Round: 54 Ground: Hardcourt outdoor
| ITF M25 Champaign | 2021/07/26 15:00 | Ryan Shane v Alexander Petrov | 6-4,6-2 |
| ITF M15 Champaign | 2021/06/21 15:00 | Alexander Petrov v Jose Pereira | 2-6,0-6 |
| ITF M25 Champaign | 2021/07/26 15:00 | Connor Farren v Toby D. Boyer | 6-2,6-3 |
| ITF M15 Edwardsville | 2021/07/20 15:30 | Ryan Shane v Toby D. Boyer | 6-2,6-7,10-7 |
| ITF M15 Edwardsville | 2021/07/19 15:00 | Brian Battistone v Toby D. Boyer | 7-6,3-6,5-10 |
| ITF M15 Heraklion | 2021/06/07 07:30 | Alec Deckers v Toby D. Boyer | 7-6,6-1 |
| ITF M15 Heraklion | 2021/06/01 06:30 | Toby D. Boyer v Matteo De Vincentis | 2-6,3-6 |
| ITF M15 Heraklion | 2021/05/31 06:30 | Petr Hajek v Toby D. Boyer | 4-6,7-6,6-10 |
| ITF M15 Heraklion | 2021/05/30 09:00 | Toby D. Boyer v Dominik Rys | 6-2,6-3 |
| ITF M15 Heraklion | 2021/05/23 12:00 | Lior Goldenberg v Toby D. Boyer | 4-6,6-3,13-11 |