Round: 25 Ground: Grass
| 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 |
| Challenger Sarasota | 2014/04/14 19:20 | Frank Dancevic v Tim Smyczek | 5-7,6-3,7-5 |
| ATP Miami Qual | 2014/03/17 15:35 | Daniel Evans v Tim Smyczek | 6-4,6-2 |
| ATP Delray Beach | 2014/02/18 16:00 | Kevin Anderson v Tim Smyczek | 4-6,6-1,6-3 |
| Challenger Leon | 2014/04/04 20:00 | Sam Groth v Austin Krajicek | 7-6,3-6,7-6 |
| Challenger Leon | 2014/04/02 22:00 | Austin Krajicek v Dustin Brown | 6-3,6-4 |
| Challenger Leon | 2014/04/01 19:20 | Austin Krajicek v Richard Gabb | 6-3,6-1 |