| Challenger Ortisei | 10/09 17:50 | 25 | [149] Sergiy Stakhovsky v Simone Bolelli [150] | 6-7,3-6 | |
| Challenger Florence | 10/02 08:00 | 25 | Lorenzo Giustino v Simone Bolelli | Cancelled | |
| Challenger Sibiu | 09/20 10:05 | 26 | [147] Simone Bolelli v Jelle Sels [338] | 6-7,3-6 | |
| Challenger Sibiu | 09/18 10:00 | 25 | [147] Simone Bolelli v Jeremy Jahn [469] | 6-4,6-4 | |
| Challenger Szczecin | 09/12 12:20 | 26 | [145] Simone Bolelli v Rogerio Dutra Silva [149] | 2-6,4-6 | |
| Challenger Szczecin | 09/10 13:50 | 25 | [145] Simone Bolelli v Kenny de Schepper [180] | 7-5,4-6,6-2 | |
| US Open | 08/23 15:00 | 45 | [242] Donald Young v Simone Bolelli [144] | 0-6,6-4,6-2 | |
| US Open | 08/21 22:50 | 44 | [254] Maxmilian Neuchrist v Simone Bolelli [144] | 5-7,7-5,5-7 | |
| Challenger Pullach | 08/06 13:05 | 25 | [143] Simone Bolelli v Sebastian Ofner [210] | 3-6,4-6 | |
| Challenger Padova | 07/25 17:00 | 25 | Edoardo Eremin v Simone Bolelli | 6-1,3-6,6-2 | |
| ATP Bastad | 07/20 14:30 | 27 | [153] Simone Bolelli v Henri Laaksonen [148] | 6-3,2-6,4-6 | |
| ATP Bastad | 07/18 10:20 | 26 | [12] Diego Schwartzman v Simone Bolelli [153] | 6-7,3-6 | |
| ATP Bastad | 07/17 11:35 | 25 | Roberto Carballes Baena v Simone Bolelli | 6-4,3-6,4-6 | |
| ATP Bastad Qual | 07/16 09:00 | 164 | [153] Simone Bolelli v Viktor Galovic [277] | 6-4,6-2 | |
| ATP Bastad Qual | 07/15 09:40 | 64 | [154] Simone Bolelli v Pedro Martinez [251] | 6-2,6-3 | |
| Wimbledon | 07/05 17:00 | 24 | [154] Simone Bolelli v Fabio Fognini [16] | 3-6,4-6,1-6 | |
| Wimbledon | 07/03 12:55 | 23 | [76] Pablo Cuevas v Simone Bolelli [154] | 6-7,6-7,1-6 | |
| Wimbledon Qual | 06/28 11:35 | 45 | [153] Simone Bolelli v Bradley Klahn [170] | 3-6,4-6,6-7 | |
| Wimbledon Qual | 06/26 16:55 | 45 | [153] Simone Bolelli v Viktor Galovic [183] | 7-6,6-3 | |
| Wimbledon Qual | 06/25 15:30 | 44 | [125] Ramkumar Ramanathan v Simone Bolelli [153] | 3-6,4-6 | |
| ATP Queens Qual | 06/16 10:00 | 64 | [59] Julien Benneteau v Simone Bolelli [148] | 7-6,4-6,7-5 | |
| French Open | 05/28 15:45 | 23 | [1] Rafael Nadal v Simone Bolelli [129] | 6-4,6-3,7-6 | |
| French Open Qual | 05/25 10:25 | 46 | [312] Santiago Giraldo v Simone Bolelli [130] | 6-0,6-2 | |
| French Open Qual | 05/24 08:00 | 45 | [234] Yasutaka Uchiyama v Simone Bolelli [130] | 6-7,3-6 | |
| French Open Qual | 05/22 09:55 | 44 | [168] Tommy Robredo v Simone Bolelli [130] | 4-6,4-6 | |
| Challenger Rome | 05/10 15:00 | 27 | Simone Bolelli v Laslo Djere | Walkover | |
| Challenger Rome | 05/09 11:50 | 26 | [139] Simone Bolelli v Mohamed Safwat [183] | 6-1,6-4 | |
| Challenger Rome | 05/09 08:00 | 25 | [139] Simone Bolelli v Marco Trungelliti [172] | 6-2,7-6 | |
| ATP Estoril | 05/04 17:00 | 27 | [153] Simone Bolelli v Frances Tiafoe [64] | 5-7,2-6 | |
| ATP Estoril | 05/02 18:50 | 26 | [79] Federico Delbonis v Simone Bolelli [153] | 6-3,5-7,2-6 |