Round: 44 Ground: Clay
| Challenger Bastad Qual | 2016/07/02 10:00 | Esteban Bruna v Lucas Renard | 0-6,2-6 |
| ITF Colombia F2 | 2016/06/20 15:00 | Roberto Cid Subervi v Esteban Bruna | 6-2,6-0 |
| ITF Colombia F2 | 2016/06/19 15:00 | Boris Arias v Esteban Bruna | 6-4,3-6,3-6 |
| ITF Colombia F1 | 2016/06/14 21:20 | Esteban Bruna v Luis Valero | 4-6,4-6 |
| ITF Colombia F1 | 2016/06/13 15:00 | Esteban Bruna v Tomas Builes | 6-1,6-4 |
| ITF Colombia F1 | 2016/06/12 15:00 | Esteban Bruna v Rodrigo Echavarria | 6-2,6-2 |
| ITF Argentina F9 | 2016/05/30 22:00 | Alejo Vilaro v Esteban Bruna | 6-2,6-0 |
| ITF Argentina F9 | 2016/05/28 22:00 | Asdrubal Gobernate v Esteban Bruna | 5-7,6-4,1-6 |
| ITF Germany F6 | 2016/07/06 11:25 | Leonard Von Hindte v Vincent Jaensch-Mueller | 3-6,4-6 |
| ITF Germany F6 | 2016/07/04 10:00 | Leonard Von Hindte v Milan Welte | 6-0,6-1 |
| ITF Germany F6 | 2016/07/03 12:00 | Adrian Obert v Leonard Von Hindte | 1-6,1-6 |
| ITF Netherlands F3 | 2016/06/25 10:00 | Leonard Von Hindte v Jake Douglas | 2-6,1-6 |
| ITF Germany F4 | 2016/06/21 12:00 | Benjamin Bonzi v Leonard Von Hindte | 6-1,6-4 |
| ITF Italy F7 | 2016/04/18 10:15 | Leonard Von Hindte v Tim Van Rijthoven | 0-6,2-6 |
| ITF Italy F7 Qual | 2016/04/17 08:00 | Leonard Von Hindte v Giuliano Benedetti | 6-1,7-6 |
| ITF Italy F7 Qual | 2016/04/16 07:30 | Manuel Mazzella v Leonard Von Hindte | 6-7,1-6 |