Round: 28 Ground: Hardcourt outdoor
| ITF Great Britain F6 | 2016/11/09 10:00 | Scott Clayton v Jonathan Gray | 6-0,6-4 |
| ITF Great Britain F5 | 2016/11/01 14:10 | Jonathan Gray v Scott Clayton | 6-4,3-6,4-6 |
| ITF Egypt F30 | 2016/10/26 08:00 | Jonathan Gray v David Hopkins | 2-6,4-6 |
| ITF Egypt F29 | 2016/10/19 11:55 | Robbie Ridout v Jonathan Gray | 6-3,6-3 |
| ITF Egypt F28 | 2016/10/12 14:30 | Jonathan Gray v Andrea Vavassori | 1-6,2-6 |
| ITF Egypt F28 Qual | 2016/10/10 14:00 | Jonathan Gray v Georg Winkler | 6-2,6-3 |
| ITF Egypt F27 | 2016/10/06 17:35 | Petr Hajek v Jonathan Gray | 7-6,5-7,6-2 |
| ITF Egypt F27 | 2016/10/05 17:10 | Sagar Ahuja v Jonathan Gray | 0-6,0-6 |
| Challenger Knoxville | 2016/11/09 22:15 | Brydan Klein v Frances Tiafoe | 6-3,5-7,1-6 |
| Challenger Charlottesville | 2016/10/31 17:45 | Tennys Sandgren v Brydan Klein | 6-4,6-7,6-1 |
| Challenger Las Vegas | 2016/10/21 20:05 | Sekou Bangoura v Brydan Klein | 6-4,3-6,6-4 |
| Challenger Las Vegas | 2016/10/19 17:30 | Zhe Li v Brydan Klein | 1-6,6-1,3-6 |
| Challenger Las Vegas | 2016/10/18 20:45 | Brydan Klein v Frances Tiafoe | 2-6,7-5,6-3 |
| Challenger Fairfield | 2016/10/15 21:10 | Quentin Halys v Brydan Klein | 6-2,6-4 |
| Challenger Fairfield | 2016/10/15 17:00 | Brydan Klein v Tommy Paul | 7-6,3-6,6-1 |
| Challenger Fairfield | 2016/10/13 18:00 | Ruben Bemelmans v Brydan Klein | 3-6,7-5,6-7 |