Stadium: Centre Court Round: 26 Ground: Clay
| Challenger Banja Luka | 2018/09/11 08:00 | Dimitar Kuzmanov v Ante Pavic | 6-1,7-6 |
| ITF Poland F8 | 2018/08/26 10:00 | Dimitar Kuzmanov v Gijs Brouwer | 6-4,6-1 |
| ITF Poland F8 | 2018/08/25 11:40 | Dimitar Kuzmanov v Artem Smirnov | 7-5,6-1 |
| ITF Poland F8 | 2018/08/24 12:30 | Dimitar Kuzmanov v Pawel Juszczak | 6-1,7-6 |
| ITF Poland F8 | 2018/08/22 09:00 | Dimitar Kuzmanov v Karol Drzewiecki | 6-2,6-4 |
| ITF Poland F8 | 2018/08/21 08:00 | Dimitar Kuzmanov v Vitalii Shcherba | 6-0,6-0 |
| Challenger Meerbusch | 2018/08/15 12:25 | Dimitar Kuzmanov v Nicola Kuhn | 4-6,4-6 |
| Challenger Meerbusch | 2018/08/13 10:20 | Gleb Sakharov v Dimitar Kuzmanov | 3-6,0-6 |
| Challenger Banja Luka | 2018/09/11 11:05 | Alessandro Giannessi v Andrej Martin | 6-4,4-6,6-4 |
| Challenger Seville | 2018/09/03 18:30 | Alejandro Davidovich Fokina v Alessandro Giannessi | 6-7,6-4,7-6 |
| Challenger Como | 2018/08/27 15:30 | Martin Klizan v Alessandro Giannessi | 6-2,6-4 |
| US Open | 2018/08/21 19:05 | Alessandro Giannessi v Constant Lestienne | 3-6,2-6 |
| Challenger Scheveningen | 2018/07/20 17:35 | Alessandro Giannessi v Thiemo De Bakker | 6-3,6-7,4-6 |
| Challenger Scheveningen | 2018/07/18 10:30 | Dustin Brown v Alessandro Giannessi | 6-4,2-6,3-6 |
| Challenger Scheveningen | 2018/07/16 11:30 | Alessandro Giannessi v Tsung-Hua Yang | 3-6,6-1,6-3 |
| Challenger Perugia | 2018/07/13 19:00 | Alessandro Giannessi v Salvatore Caruso | 6-4,4-6,4-6 |