Round: 25 Ground: Hardcourt outdoor
| Challenger Tiburon | 2014/10/06 19:40 | Kyle Edmund v Mcgee, James | 6-3,3-6,3-6 |
| Challenger Shanghai | 2014/09/03 05:35 | Yang, Tsung-Hua v Kyle Edmund | 7-5,6-2 |
| Segovia, Spain | 2014/08/01 14:20 | Menendez-Maceiras, Adrian v Kyle Edmund | 4-6,6-4,7-6 |
| Segovia, Spain | 2014/07/31 15:50 | Kyle Edmund v Ortega-Olmedo, Roberto | 6-2,6-2 |
| Challenger Recanati | 2014/07/15 19:35 | Kyle Edmund v Giner, Marc | 6-1,6-4 |
| Wimbledon, London, Great Britain | 2014/06/23 15:45 | Haider-Maurer, Andreas v Kyle Edmund | 6-3,7-6,6-2 |
| ATP - Miami | 2014/03/19 18:20 | Benneteau, Julien v Kyle Edmund | 6-7,6-3,6-2 |
| ITF USA F8 | 2014/03/13 18:00 | Kyle Edmund v Bangoura, Sekou | 6-3,3-6,2-6 |
| Challenger Tiburon | 2014/10/09 19:00 | Marcos Giron v Klahn, Bradley | 7-6,7-6 |
| Challenger Tiburon | 2014/10/07 18:10 | Tennys Sandgren v Klahn, Bradley | 4-6,6-7 |
| US Open, New York, USA | 2014/08/25 21:20 | Klahn, Bradley v Andrey Kuznetsov | 4-6,6-4,3-6,5-7 |
| Wimbledon, London, Great Britain | 2014/06/23 16:35 | Klahn, Bradley v Querrey, Sam | 7-6,4-6,1-6,5-7 |
| ATP - Miami | 2014/03/20 18:40 | Klahn, Bradley v Garcia-Lopez, Guillermo | 6-1,1-6,4-6 |