Round: 25 Ground: Clay
| Challenger Biella | 2018/09/18 11:45 | Roberto Carballes Baena v Lorenzo Giustino | 6-3,6-4 |
| Challenger Szczecin | 2018/09/13 12:45 | Alexey Vatutin v Lorenzo Giustino | 6-7,6-1,6-0 |
| Challenger Szczecin | 2018/09/11 16:00 | Lorenzo Giustino v Dustin Brown | 6-7,6-1,7-6 |
| Challenger Seville | 2018/09/05 09:00 | Lorenzo Giustino v Sergio Gutierrez-Ferrol | 7-5,3-6,3-6 |
| Challenger Seville | 2018/09/04 08:30 | Lorenzo Giustino v Federico Gaio | 6-4,6-2 |
| Challenger Como | 2018/08/29 11:45 | Viktor Galovic v Lorenzo Giustino | 4-6,7-5,7-5 |
| Challenger Como | 2018/08/28 08:00 | Lorenzo Giustino v Stephane Robert | 6-2,6-1 |
| US Open | 2018/08/24 15:00 | Lorenzo Giustino v Dennis Novak | 5-7,4-6 |
| Challenger Sibiu | 2018/09/20 10:05 | Simone Bolelli v Jelle Sels | 6-7,3-6 |
| Challenger Sibiu | 2018/09/18 10:00 | Simone Bolelli v Jeremy Jahn | 6-4,6-4 |
| Challenger Szczecin | 2018/09/12 12:20 | Simone Bolelli v Rogerio Dutra Silva | 2-6,4-6 |
| Challenger Szczecin | 2018/09/10 13:50 | Simone Bolelli v Kenny de Schepper | 7-5,4-6,6-2 |
| US Open | 2018/08/23 15:00 | Donald Young v Simone Bolelli | 0-6,6-4,6-2 |
| US Open | 2018/08/21 22:50 | Maximilian Neuchrist v Simone Bolelli | 5-7,7-5,5-7 |
| Challenger Pullach | 2018/08/06 13:05 | Simone Bolelli v Sebastian Ofner | 3-6,4-6 |
| Challenger Padova | 2018/07/25 17:00 | Edoardo Eremin v Simone Bolelli | 6-1,3-6,6-2 |