Round: 26 Ground: Hardcourt indoor
| Challenger Tiburon | 2014/10/07 23:00 | Ryan Harrison v Tim Smyczek | 3-6,3-6 |
| Challenger Dallas | 2015/02/04 00:10 | Tim Smyczek v James McGee | 3-6,6-4,7-5 |
| 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 Dallas | 2015/02/04 04:00 | Rhyne Williams v Ryan Harrison | 6-7,2-6 |
| Challenger Knoxville | 2014/11/05 23:30 | Ryan Harrison v Adrian Mannarino | 1-6,1-6 |
| Challenger Charlottesville | 2014/10/31 20:50 | Ryan Harrison v Liam Broady | 7-6,6-7,3-6 |
| Challenger Charlottesville | 2014/10/30 22:35 | Daniel Nguyen v Ryan Harrison | 1-6,4-6 |
| Challenger Charlottesville | 2014/10/28 23:50 | Ryan Harrison v Mitchell Frank | 6-4,6-1 |
| Challenger Tiburon | 2014/10/07 23:00 | Ryan Harrison v Tim Smyczek | 3-6,3-6 |
| US Open | 2014/08/27 21:00 | Grigor Dimitrov v Ryan Harrison | 6-2,7-6,6-2 |
| Wimbledon | 2014/06/23 13:55 | Grigor Dimitrov v Ryan Harrison | 7-6,6-3,6-2 |