Round: 60 Ground: Clay
| USA F34, Singles | 2016/10/22 20:00 | Ton, Andrew v Douglas, Jake | 7-6,0-6,6-2 |
| ITF USA F29 | 2016/09/21 17:00 | Redlicki, Martin v Douglas, Jake | 6-0,6-3 |
| ITF USA F29 | 2016/09/18 18:30 | Rivera, Cristobal v Douglas, Jake | 3-6,4-6 |
| ITF USA F29 | 2016/09/16 23:00 | Vance, Jack v Douglas, Jake | 1-6,1-6 |
| ITF USA F28 | 2016/09/14 20:20 | Brymer, Gage v Douglas, Jake | 6-4,6-2 |
| ITF USA F28 | 2016/09/12 17:00 | Douglas, Jake v Kushnirovich, Gary | 6-7,6-4,6-1 |
| ITF USA F28 | 2016/09/11 18:00 | Douglas, Jake v Gabriel Roveri Sidney | 6-1,6-0 |
| ITF USA F28 | 2016/09/10 18:00 | Douglas, Jake v Davidson, Patrick | 6-0,7-6 |
| ITF USA F31 Qual | 2016/10/09 14:00 | Rakic, Strahinja v Bettendroffer, Kevin | 6-1,6-7,2-6 |
| ITF USA F31 Qual | 2016/10/08 17:00 | Chang, Jonathan v Rakic, Strahinja | 6-3,3-6,3-6 |
| ITF Serbia F2 | 2016/07/28 12:45 | Mesaros, Kristijan v Rakic, Strahinja | 6-3,1-6,6-2 |
| ITF Serbia F2 | 2016/07/26 10:00 | Rakic, Strahinja v Markovic, Goran | 6-3,0-6,7-6 |
| ITF Serbia F1 Qual | 2016/07/16 10:00 | Rakic, Strahinja v Aramburu, Aitor | 6-1,7-6 |
| ITF Macedonia F1 | 2016/07/05 10:10 | Rakic, Strahinja v Hampel, Lenny | 1-6,2-6 |
| ITF Macedonia F1 | 2016/07/04 10:50 | Domagoj Biljesko v Rakic, Strahinja | 3-6,4-6 |
| ITF Macedonia F2 | 2016/06/26 12:00 | Hirschmueller, Christian v Rakic, Strahinja | 6-4,6-1 |