Round: 25 Ground: Hardcourt outdoor
| 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 |
| Wimbledon Qual | 2014/06/19 11:50 | Daniel Brands v Ryan Harrison | 6-7,2-6,3-6 |
| Wimbledon Qual | 2014/06/16 10:00 | Taro Daniel v Ryan Harrison | 6-2,3-6,4-6 |
| Challenger Bordeaux | 2014/05/13 08:00 | Juan Ignacio Londero v Ryan Harrison | 6-3,2-6,6-4 |
| ATP Madrid Qual | 2014/05/03 09:00 | Julien Benneteau v Ryan Harrison | 3-6,4-6 |
| ATP Houston | 2014/04/08 18:40 | Ryan Harrison v Donald Young | 0-6,1-6 |
| ATP Houston Qual | 2014/04/07 18:20 | Ryan Harrison v Ruben Bemelmans | 1-6,7-5,7-6 |
| US Open | 2014/08/29 19:40 | Tim Smyczek v Roberto Bautista-Agut | 3-6,2-6,1-6 |
| US Open | 2014/08/26 19:40 | Filip Krajinovic v Tim Smyczek | 6-4,3-6,2-6,6-7 |
| ATP Washington | 2014/08/01 00:05 | Tim Smyczek v Richard Gasquet | 3-6,2-6 |
| ATP Washington | 2014/07/30 01:45 | Jeremy Chardy v Tim Smyczek | 6-7,6-3,4-6 |
| ATP Newport | 2014/07/08 17:40 | Tim Smyczek v Austin Krajicek | 6-7,1-6 |
| Wimbledon Qual | 2014/06/16 10:00 | Tim Smyczek v Niels Desein | 6-3,6-2 |
| Challenger Tallahassee | 2014/04/28 15:00 | Yoshihito Nishioka v Tim Smyczek | 6-2,6-2 |
| Challenger Savannah | 2014/04/21 18:55 | Tim Smyczek v Facundo Bagnis | 6-7,3-6 |