| UTR Pro Winston-Salem | 06/08 15:50 | 53 | Vincent Gillespie v Ian Mayew | Walkover | |
| UTR Pro Winston-Salem | 06/07 18:25 | 28 | Vincent Gillespie v Agustin Mastri | 6-4,3-6,2-6 | |
| UTR Pro Winston-Salem | 06/06 18:40 | - | Vincent Gillespie v Tygen Goldammer | 6-4,6-2 | |
| UTR Pro Winston-Salem | 06/06 02:00 | - | Vincent Gillespie v Marshall Landry | 6-3,6-2 | |
| UTR Pro Winston-Salem | 06/05 22:35 | - | Nathan Pitts v Vincent Gillespie | 6-7,6-3,2-6 | |
| UTR Pro Winston-Salem | 12/06 18:30 | - | Dhakshineswar Suresh v Vincent Gillespie | 6-1,6-6 | |
| UTR Pro Winston-Salem | 12/04 16:00 | - | Vincent Gillespie v Franco Capalbo | 6-3,6-3 |