| Challenger Istanbul | 09/12 07:30 | 25 | [174] Aldin Setkic v Simone Bolelli [204] | 2-6,3-6 | |
| US Open Qual | 08/25 15:00 | 46 | [218] Simone Bolelli v Vincent Millot [164] | 6-1,4-6,3-6 | |
| US Open Qual | 08/24 15:00 | 45 | [110] Casper Ruud v Simone Bolelli [218] | 2-6,4-6 | |
| US Open Qual | 08/22 21:35 | 44 | [218] Simone Bolelli v Daniel Brands [201] | 6-2,6-3 | |
| Challenger Scheveningen | 07/21 12:35 | 27 | [96] Ruben Bemelmans v Simone Bolelli [230] | 6-2,6-4 | |
| Challenger Scheveningen | 07/19 14:20 | 26 | [230] Simone Bolelli v Sergiy Stakhovsky [114] | 6-4,3-6,6-3 | |
| Challenger Scheveningen | 07/17 16:30 | 25 | Michiel de Krom v Simone Bolelli | 0-6,3-6 | |
| Wimbledon | 07/05 11:50 | 24 | [10] Jo-Wilfried Tsonga v Simone Bolelli [313] | 6-1,7-5,6-2 | |
| Wimbledon | 07/03 10:30 | 23 | [312] Simone Bolelli v Yen-Hsun Lu [75] | 6-3,1-6,6-3,6-4 | |
| Wimbledon Qual | 06/30 10:00 | - | [153] Pedro Sousa v Simone Bolelli [312] | 2-6,3-6,2-6 | |
| Wimbledon Qual | 06/28 17:50 | 45 | [312] Simone Bolelli v Adrian M-Maceiras [145] | 6-4,6-4 | |
| Wimbledon Qual | 06/26 13:20 | 44 | [187] Sam Groth v Simone Bolelli [312] | 6-7,6-2,9-11 | |
| Challenger Todi | 06/22 16:10 | 26 | [104] Facundo Bagnis v Simone Bolelli [316] | 6-3,2-6,6-2 | |
| Challenger Todi | 06/20 18:30 | 25 | [316] Simone Bolelli v Carlos Taberner [303] | 7-6,6-2 | |
| Challenger Caltanissetta | 06/14 19:40 | 26 | [331] Simone Bolelli v Tennys Sandgren [100] | 6-3,4-6,4-6 | |
| Challenger Caltanissetta | 06/13 15:40 | 25 | [331] Simone Bolelli v Joao Pedro Sorgi [292] | 7-5,6-2 | |
| French Open | 05/31 09:00 | 24 | [7] Dominic Thiem v Simone Bolelli [470] | 7-5,6-1,6-3 | |
| French Open | 05/29 12:00 | 23 | [470] Simone Bolelli v Nicolas Mahut [48] | 6-4,6-2,6-2 | |
| French Open Qual | 05/25 12:15 | 46 | [104] Marco Cecchinato v Simone Bolelli [463] | 4-6,4-6 | |
| French Open Qual | 05/24 13:05 | 45 | [463] Simone Bolelli v Maximilian Marterer [130] | 6-3,1-6,6-4 | |
| French Open Qual | 05/22 08:00 | 44 | [463] Simone Bolelli v Christian Garin [200] | 7-6,4-6,7-6 | |
| Challenger Ostrava | 05/05 11:20 | 27 | [339] Simone Bolelli v Attila Balazs [264] | 7-6,3-6,4-6 | |
| Challenger Ostrava | 05/03 11:55 | 26 | [272] Sebastian Ofner v Simone Bolelli [339] | 5-7,1-6 | |
| Challenger Ostrava | 05/01 13:30 | 25 | [339] Simone Bolelli v Constant Lestienne [256] | Retired | |
| Challenger Francavilla | 04/25 13:00 | 25 | [224] Matteo Donati v Simone Bolelli [342] | 4-6,7-6,7-5 | |
| ATP Monte Carlo Qual | 04/16 09:00 | 46 | [341] Simone Bolelli v Renzo Olivo [92] | 4-6,7-6,2-6 | |
| ATP Monte Carlo Qual | 04/15 09:00 | 45 | [77] Mikhail Kukushkin v Simone Bolelli [341] | 3-6,2-6 | |
| Challenger St Brieuc | 03/30 11:25 | 26 | [404] Egor Gerasimov v Simone Bolelli [346] | 6-7,6-4,6-3 | |
| Challenger St Brieuc | 03/28 12:20 | 25 | [346] Simone Bolelli v Daniel Brands [209] | 6-4,6-3 | |
| Challenger Santiago | 03/10 21:45 | 28 | [85] Rogerio Dutra Silva v Simone Bolelli [349] | 6-4,6-2 |