Round: 60 Ground: Clay
| Challenger - Charlottesville - Qualificação | 2016/10/29 17:40 | Alan Gadjiev v Tucker Vorster | 4-6,7-6,3-6 |
| Challenger Columbus - Qualificação | 2016/09/17 20:30 | Alan Gadjiev v Damon Gooch | 5-7,0-6 |
| Challenger Cary - Qual. | 2016/09/10 17:25 | Alan Gadjiev v Arturo Schmidt | 4-6,3-6 |
| ITF - Egipto F17 | 2016/07/26 16:00 | Yurii Dzhavakian v Alan Gadjiev | 4-6,4-6 |
| ITF - Egipto F16 | 2016/07/23 16:00 | Alan Gadjiev v Benjamin Lock | 1-6,4-6 |
| ITF - Egipto F16 | 2016/07/22 16:00 | Majed Kilani v Alan Gadjiev | 4-6,7-6,2-6 |
| ITF - Egipto F16 | 2016/07/21 17:50 | Zeljko Milovic v Alan Gadjiev | 6-7,2-6 |
| ITF - Egipto F16 | 2016/07/20 16:00 | Alan Gadjiev v Mohamed Aziz Dougaz | 6-4,1-6,7-6 |
| ITF - República Dominicana F2 | 2017/12/04 13:00 | Andres Urrea v Ian Dempster | 7-6,3-6,6-1 |
| ITF - República Dominicana F2 | 2017/12/03 14:00 | Ian Dempster v Lucas Bouquet | 6-4,6-2 |
| ITF - República Dominicana F1 | 2017/11/28 17:55 | Matthias Haim v Ian Dempster | 6-4,6-4 |
| ITF - República Dominicana F1 | 2017/11/27 13:00 | Herbert Jody Maginley v Ian Dempster | 4-6,4-6 |
| ITF - República Dominicana F1 | 2017/11/25 14:00 | Beauregard Treyz v Ian Dempster | 3-6,2-6 |
| ITF - EUA F33 - Qualificação | 2017/10/07 16:30 | Ian Dempster v Guillermo Arrambide | 4-6,2-6 |
| ITF - México F5 | 2016/05/31 20:05 | Ian Dempster v Andrew Carter | 0-6,2-6 |
| ITF - México F5 | 2016/05/30 15:30 | Juan Jose Mateus Rubiano v Ian Dempster | 2-6,6-7 |