Round: 60 Ground: Clay
| ITF USA F29 | 2016/09/21 17:00 | Martin Redlicki v Jake Douglas | 6-0,6-3 |
| ITF USA F29 | 2016/09/18 18:30 | Cristobal Rivera v Jake Douglas | 3-6,4-6 |
| ITF USA F29 | 2016/09/16 23:00 | Jack Vance v Jake Douglas | 1-6,1-6 |
| ITF USA F28 | 2016/09/14 20:20 | Gage Brymer v Jake Douglas | 6-4,6-2 |
| ITF USA F28 | 2016/09/12 17:00 | Jake Douglas v Gary Kushnirovich | 6-7,6-4,6-1 |
| ITF USA F28 | 2016/09/11 18:00 | Jake Douglas v Gabriel Roveri Sidney | 6-1,6-0 |
| ITF USA F28 | 2016/09/10 18:00 | Jake Douglas v Patrick Davidson | 6-0,7-6 |
| ITF Netherlands F4 | 2016/07/03 08:00 | Marc Dijkhuizen v Jake Douglas | 6-4,0-6,7-5 |
| ITF Serbia F2 | 2016/07/28 12:45 | Kristijan Mesaros v Strahinja Rakic | 6-3,1-6,6-2 |
| ITF Serbia F2 | 2016/07/26 10:00 | Strahinja Rakic v Goran Markovic | 6-3,0-6,7-6 |
| ITF Serbia F1 Qual | 2016/07/16 10:00 | Strahinja Rakic v Aitor Aramburu | 6-1,7-6 |
| ITF Macedonia F1 | 2016/07/05 10:10 | Strahinja Rakic v Lenny Hampel | 1-6,2-6 |
| ITF Macedonia F1 | 2016/07/04 10:50 | Domagoj Biljesko v Strahinja Rakic | 3-6,4-6 |
| ITF Macedonia F2 | 2016/06/26 12:00 | Christian Hirschmueller v Strahinja Rakic | 6-4,6-1 |
| ITF Macedonia F1 | 2016/06/21 14:00 | Strahinja Rakic v Giorgio Ricca | 6-4,3-6,2-6 |
| ITF Macedonia F1 Qual | 2016/06/20 08:00 | Strahinja Rakic v Keisuke Numajiri | 6-3,6-2 |