Round: 25 Ground: Hardcourt indoor
| Challenger Knoxville | 2014/11/08 21:15 | Tim Smyczek v Sam Groth | 3-6,4-6 |
| Challenger Knoxville | 2014/11/07 23:00 | Malek Jaziri v Tim Smyczek | 6-7,3-6 |
| Challenger Knoxville | 2014/11/06 22:30 | Jared Donaldson v Tim Smyczek | 0-6,4-6 |
| Challenger Knoxville | 2014/11/04 23:10 | Hunter Reese v Tim Smyczek | 3-6,1-6 |
| Challenger Charlottesville | 2014/10/28 21:00 | Liam Broady v Tim Smyczek | 4-6,6-2,6-4 |
| Challenger Tiburon | 2014/10/10 20:20 | John Millman v Tim Smyczek | 6-1,5-7,6-3 |
| Challenger Tiburon | 2014/10/09 22:00 | Jared Donaldson v Tim Smyczek | 6-2,6-7,5-7 |
| Challenger Tiburon | 2014/10/07 23:00 | Ryan Harrison v Tim Smyczek | 3-6,3-6 |
| Challenger Knoxville | 2014/11/06 17:20 | James McGee v Adrian Mannarino | 3-6,2-6 |
| Challenger Knoxville | 2014/11/05 19:10 | Marcelo Arevalo v James McGee | 3-6,2-6 |
| Challenger Charlottesville | 2014/10/28 14:00 | Tennys Sandgren v James McGee | 6-3,6-1 |
| Challenger Tiburon | 2014/10/10 22:50 | Sam Querrey v James McGee | 6-1,7-5 |
| Challenger Tiburon | 2014/10/08 22:00 | James McGee v Jordan Thompson | 7-6,6-3 |
| Challenger Tiburon | 2014/10/06 19:40 | Kyle Edmund v James McGee | 6-3,3-6,3-6 |
| US Open | 2014/08/25 18:05 | James McGee v Aleksandr Nedovyesov | 6-4,2-6,1-6,6-7 |
| US Open - Qual. | 2014/08/22 17:30 | Ze Zhang v James McGee | 6-0,4-6,4-6 |