Round: 27 Ground: Hardcourt outdoor
| Challenger Granby | 2014/07/17 18:30 | Lukas Lacko v Richard Gabb | 6-3,1-6,2-6 |
| Challenger Granby | 2014/07/15 16:05 | Pavel Krainik v Richard Gabb | 4-6,5-7 |
| ITF Korea F1 | 2014/04/24 02:45 | Richard Gabb v Frederik Nielsen | 1-6,6-3,1-6 |
| ITF Korea F1 | 2014/04/22 01:00 | Richard Gabb v Daniel Nguyen | 6-1,6-3 |
| Challenger Leon | 2014/04/01 19:20 | Austin Krajicek v Richard Gabb | 6-3,6-1 |
| Challenger Leon Qual | 2014/03/31 17:00 | Richard Gabb v Purav Raja | 3-6,6-2,2-6 |
| ITF Canada F2 | 2014/03/12 22:30 | Raheel Manji v Richard Gabb | 4-6,4-6 |
| ITF Canada F1 | 2014/03/08 00:00 | Richard Gabb v Germain Gigounon | 6-4,6-2 |
| Challenger Granby | 2014/07/17 17:00 | Eric Quigley v James McGee | 4-6,2-6 |
| ATP Newport Qual | 2014/07/06 19:45 | Ante Pavic v James McGee | 6-2,4-6,7-6 |
| ATP Newport Qual | 2014/07/05 19:00 | Michael Venus v James McGee | 6-4,6-7,2-6 |
| Wimbledon Qual | 2014/06/16 10:00 | James McGee v Aljaz Bedene | 4-6,4-6 |
| Challenger Tallahassee | 2014/05/02 14:00 | James McGee v Yoshihito Nishioka | 7-6,7-5 |
| Challenger Tallahassee | 2014/05/01 15:45 | James McGee v Mitchell Krueger | 6-2,6-2 |
| Challenger Tallahassee | 2014/04/30 16:25 | Bjorn Fratangelo v James McGee | 2-6,4-6 |
| Challenger Savannah | 2014/04/22 19:15 | Filip Krajinovic v James McGee | 6-3,6-4 |