| Challenger Santiago | 03/09 21:00 | 27 | [119] Taro Daniel v Simone Bolelli [349] | 4-6,4-6 | |
| Challenger Santiago | 03/08 19:50 | 26 | [141] Leonardo Mayer v Simone Bolelli [349] | 6-7,6-4,3-6 | |
| Challenger Santiago | 03/07 23:30 | 25 | [349] Simone Bolelli v Alessandro Giannessi [121] | Retired | |
| ATP Buenos Aires Qual | 02/11 19:55 | 45 | Dusan Lajovic v Simone Bolelli | 6-1,6-4 | |
| French Open | 05/22 11:45 | 23 | Kei Nishikori v Simone Bolelli | 6-1,7-5,6-3 | |
| ATP Marrakech | 04/06 16:10 | 26 | Borna Coric v Simone Bolelli | Walkover | |
| ATP Marrakech | 04/05 13:50 | 25 | Simone Bolelli v Taro Daniel | 7-5,6-4 | |
| ATP Miami | 03/23 22:50 | 23 | Taylor Fritz v Simone Bolelli | 6-4,6-2 | |
| Challenger Shanghai | 10/13 05:30 | 24 | Simone Bolelli v Vasek Pospisil | 3-6,4-6 | |
| Challenger Shanghai | 10/10 04:00 | 45 | Simone Bolelli v Matteo Donati | 6-4,6-3 | |
| Davis Cup | 09/18 07:00 | 1 | Teymuraz Gabashvili v Simone Bolelli | 7-6,6-1,6-3 | |
| US Open | 08/31 15:00 | 23 | Simone Bolelli v David Goffin | 4-6,1-6,2-6 | |
| Challenger Prague 2 | 08/14 11:00 | 27 | Axel Michon v Simone Bolelli | 6-2,4-6,7-6 | |
| Challenger Prague 2 | 08/13 13:05 | 26 | Roberto Carballes Baena v Simone Bolelli | 3-6,6-7 | |
| ATP Hamburg | 07/31 14:55 | 27 | Andreas Seppi v Simone Bolelli | Walkover | |
| ATP Hamburg | 07/30 16:35 | 26 | Simone Bolelli v Jaume Munar | 6-1,6-7,6-4 | |
| ATP Hamburg | 07/28 12:35 | 25 | Lukas Rosol v Simone Bolelli | 6-7,6-7 | |
| Wimbledon | 06/29 13:40 | 23 | Simone Bolelli v Kei Nishikori | 3-6,7-6,2-6,6-3,3-6 | |
| ATP Madrid | 05/07 13:15 | 26 | Rafael Nadal v Simone Bolelli | 6-2,6-2 | |
| ATP Madrid | 05/06 11:00 | 25 | Luca Vanni v Simone Bolelli | 6-4,3-6,2-6 | |
| ATP Madrid | 05/03 15:25 | 24 | Simone Bolelli v Kevin Anderson | 6-4,6-3 | |
| ATP Munich | 04/29 13:35 | 26 | Simone Bolelli v David Goffin | 6-7,7-6,1-6 | |
| ATP Munich | 04/28 15:30 | 25 | Dustin Brown v Simone Bolelli | 1-6,6-7 | |
| ATP Miami | 03/28 17:30 | 24 | Simone Bolelli v Viktor Troicki | 5-7,6-3,4-6 | |
| ATP Miami | 03/26 17:05 | 23 | Marcos Baghdatis v Simone Bolelli | 2-6,2-6 | |
| Davis Cup | 03/06 06:00 | 1 | Mikhail Kukushkin v Simone Bolelli | 7-6,6-1,6-2 | |
| Challenger Ortisei | 11/05 17:00 | 26 | Simone Bolelli v Aslan Karatsev | 4-6,3-6 | |
| ATP Geneva | 11/01 13:00 | 28 | Michal Przysiezny v Simone Bolelli | 7-6,6-4 | |
| ATP Geneva | 10/31 15:45 | 27 | Steve Darcis v Simone Bolelli | 3-6,6-2,1-6 | |
| ATP Geneva | 10/29 10:00 | 26 | Illya Marchenko v Simone Bolelli | 5-7,6-4,4-6 |