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