Round: 26 Ground: Clay
| ITF Italy F20 | 2016/07/12 10:00 | Ljubomir Celebic v Enrico Dalla Valle | 6-4,6-3 |
| ITF Macedonia F1 | 2016/07/08 10:05 | Kristijan Mesaros v Ljubomir Celebic | 6-3,6-1 |
| ITF Macedonia F1 | 2016/07/07 10:30 | Igor Saveljic v Ljubomir Celebic | 2-6,0-6 |
| ITF Macedonia F1 | 2016/07/06 08:30 | Besir Durguti v Ljubomir Celebic | 0-6,3-6 |
| ITF Macedonia F2 | 2016/06/30 08:00 | Christopher O'Connell v Ljubomir Celebic | 6-2,7-5 |
| ITF Macedonia F2 | 2016/06/29 12:10 | Dejan Katic v Ljubomir Celebic | 4-6,2-6 |
| ITF Macedonia F1 | 2016/06/21 07:30 | Ljubomir Celebic v Christopher O'Connell | 4-6,1-6 |
| ITF Italy F15 | 2016/06/14 12:55 | Patricio Heras v Ljubomir Celebic | 6-2,7-5 |
| ITF Italy F20 | 2016/07/12 12:40 | Daniele Capecchi v Federico Bertuccioli | 6-3,6-3 |
| ITF Italy F18 | 2016/07/01 14:40 | Daniele Capecchi v Antonio Massara | 5-7,6-3,3-6 |
| ITF Italy F18 | 2016/06/30 14:00 | Daniele Capecchi v Filippo Baldi | 5-7,6-1,6-3 |
| Challenger Milan Qual | 2016/06/20 08:30 | Daniele Capecchi v Lorenzo Sonego | 4-6,2-6 |
| Challenger Milan Qual | 2016/06/19 09:30 | Daniele Capecchi v Fabrizio Ornago | 6-2,6-3 |
| Challenger Milan Qual | 2016/06/18 08:00 | Michael Linzer v Daniele Capecchi | 5-7,2-6 |
| ITF Italy F15 | 2016/06/16 17:25 | Daniele Capecchi v Joao Domingues | 2-6,1-6 |
| ITF Italy F15 | 2016/06/14 11:00 | Alberto Brizzi v Daniele Capecchi | 7-6,5-7,2-6 |