| Wimbledon | 06/24 11:35 | 44 | [108] Jiri Vesely v Simone Bolelli [187] | 6-4,6-2 | |
| French Open | 05/28 13:00 | 23 | [187] Simone Bolelli v Lucas Pouille [26] | 3-6,4-6,5-7 | |
| French Open | 05/24 08:00 | 46 | [191] Simone Bolelli v Go Soeda [201] | 6-1,7-6 | |
| French Open | 05/22 16:15 | 45 | [191] Simone Bolelli v Dominik Koepfer [170] | 6-1,3-6,6-3 | |
| French Open | 05/20 15:25 | 44 | [118] Kamil Majchrzak v Simone Bolelli [191] | 5-7,6-7 | |
| Challenger Aix en Provence | 05/08 11:50 | 25 | Daniel Masur v Simone Bolelli | Cancelled | |
| ATP Estoril | 04/28 11:00 | 164 | [114] Alexei Popyrin v Simone Bolelli [162] | 2-6,6-3,6-4 | |
| ATP Estoril | 04/27 11:00 | 64 | [162] Simone Bolelli v Egor Gerasimov [136] | 6-2,7-6 | |
| Challenger Sophia Antipolis | 04/05 12:00 | 27 | [149] Simone Bolelli v Rudolf Molleker [182] | 3-6,6-3,3-6 | |
| Challenger Sophia Antipolis | 04/04 17:15 | 26 | [101] Lorenzo Sonego v Simone Bolelli [149] | 6-7,6-7 | |
| Challenger Sophia Antipolis | 04/02 09:50 | 25 | Peter Heller v Simone Bolelli | 2-6,5-7 | |
| Challenger Marbella | 03/28 16:05 | 26 | [117] Thiago Monteiro v Simone Bolelli [147] | 6-4,7-6 | |
| Challenger Marbella | 03/27 13:35 | 25 | [238] Calvin Hemery v Simone Bolelli [147] | 6-7,2-6 | |
| Challenger Pau | 02/27 17:40 | 25 | [245] Mathias Bourgue v Simone Bolelli [136] | 7-5,7-6 | |
| ATP Marseille | 02/19 13:10 | 25 | [136] Simone Bolelli v Benoit Paire [59] | 4-6,6-7 | |
| ATP Marseille | 02/18 11:00 | 164 | [227] Maxime Janvier v Simone Bolelli [136] | 4-6,5-7 | |
| ATP Marseille | 02/17 09:00 | 64 | [338] Alexandre Muller v Simone Bolelli [137] | 4-6,4-6 | |
| Challenger Cherbourg | 02/14 15:00 | 26 | [184] Mats Moraing v Simone Bolelli [137] | 6-4,7-5 | |
| Challenger Cherbourg | 02/13 19:05 | 25 | Laurent Lokoli v Simone Bolelli | 3-6,3-6 | |
| Australian Open | 01/08 23:00 | 44 | [151] Tatsuma Ito v Simone Bolelli [136] | 6-3,3-6,6-3 | |
| ATP Pune | 01/02 11:30 | 26 | [141] Simone Bolelli v Jaume Munar [81] | 5-7,0-6 | |
| ATP Pune | 01/01 09:30 | 25 | [141] Simone Bolelli v Denis Istomin [92] | 6-4,6-4 | |
| ATP Pune | 12/30 07:30 | 164 | [184] Sebastian Ofner v Simone Bolelli [145] | 6-7,5-7 | |
| ATP Pune | 12/29 07:30 | 64 | [173] Brayden Schnur v Simone Bolelli [145] | 3-6,6-7 | |
| Challenger Mouilleron le Captif | 11/06 13:25 | 25 | [146] Simone Bolelli v Quentin Halys [145] | 6-7,6-7 | |
| Challenger Eckental | 11/01 13:00 | 26 | [145] Simone Bolelli v Daniel Masur [287] | 4-6,7-5,3-6 | |
| Challenger Eckental | 10/31 16:00 | 25 | [82] Lukas Lacko v Simone Bolelli [145] | 6-7,3-6 | |
| Challenger Brest | 10/23 12:40 | 25 | [152] Quentin Halys v Simone Bolelli [147] | 4-6,7-6,6-3 | |
| Challenger Ortisei | 10/12 11:00 | 27 | [150] Simone Bolelli v Dennis Novak [145] | 6-7,6-7 | |
| Challenger Ortisei | 10/10 14:10 | 26 | Kirill Kivattsev v Simone Bolelli | 3-6,2-6 |