Round: 62 Ground: Clay
| ITF Mexico F5 | 2016/05/31 20:05 | Ian Dempster v Andrew Carter | 0-6,2-6 |
| ITF Mexico F5 | 2016/05/30 15:30 | Juan Jose Mateus Rubiano v Ian Dempster | 2-6,6-7 |
| ITF Mexico F5 | 2016/05/29 16:00 | Wulfrano M M Esdras v Ian Dempster | 3-6,1-6 |
| ITF Mexico F5 | 2016/05/28 17:00 | Ian Dempster v Samuel Beddow | 5-7,6-4,6-2 |
| ITF Mexico F4 | 2016/05/23 15:00 | Ian Dempster v Jose Antonio Rodriguez Rodriguez | 2-6,2-6 |
| ITF Mexico F4 | 2016/05/22 15:00 | Jose Daniel Bendeck v Ian Dempster | 7-5,3-6,6-7 |
| ITF USA F19 | 2015/06/24 17:45 | Ian Dempster v Ryan Haviland | 5-7,3-6 |
| ITF USA F15 Qual | 2014/06/16 14:00 | Raymond Sarmiento v Ian Dempster | 6-4,6-1 |