Round: 26 Ground: Hardcourt indoor
| Challenger Tiburon | 2014/10/09 22:00 | Donaldson, Jared v Smyczek, Tim | 6-2,6-7,5-7 |
| Challenger Knoxville | 2014/11/04 18:15 | Nguyen, Daniel v Donaldson, Jared | 7-5,1-6,2-6 |
| Challenger Tiburon | 2014/10/09 22:00 | Donaldson, Jared v Smyczek, Tim | 6-2,6-7,5-7 |
| Challenger Tiburon | 2014/10/07 20:25 | Donaldson, Jared v Novikov, Dennis | 6-3,6-2 |
| US Open, New York, USA | 2014/08/26 22:05 | Gaël Monfils v Donaldson, Jared | 6-4,6-2,6-4 |
| Washington, USA | 2014/07/28 21:00 | Ram, Rajeev v Donaldson, Jared | 6-7,6-4,7-5 |
| ATP Washington Qual | 2014/07/26 15:55 | Donaldson, Jared v Gonzalo Lama | 6-1,6-1 |
| ITF USA F17 | 2014/06/29 16:00 | Donaldson, Jared v Harris, Andrew | 6-3,6-2 |
| ITF USA F17 | 2014/06/28 16:30 | Sarmiento, Raymond v Donaldson, Jared | 2-6,6-3,6-7 |
| Challenger Knoxville | 2014/11/04 23:10 | Reese, Hunter v Smyczek, Tim | 3-6,1-6 |
| Challenger Charlottesville | 2014/10/28 21:00 | Liam Broady v Smyczek, Tim | 4-6,6-2,6-4 |
| Challenger Tiburon | 2014/10/10 20:20 | John Millman v Smyczek, Tim | 6-1,5-7,6-3 |
| Challenger Tiburon | 2014/10/09 22:00 | Donaldson, Jared v Smyczek, Tim | 6-2,6-7,5-7 |
| Challenger Tiburon | 2014/10/07 23:00 | Harrison, Ryan v Smyczek, Tim | 3-6,3-6 |
| US Open, New York, USA | 2014/08/29 19:40 | Smyczek, Tim v Bautista-Agut, Roberto | 3-6,2-6,1-6 |
| US Open, New York, USA | 2014/08/26 19:40 | Filip Krajinovic v Smyczek, Tim | 6-4,3-6,2-6,6-7 |
| Washington, USA | 2014/08/01 00:05 | Smyczek, Tim v Richard Gasquet | 3-6,2-6 |