| ATP - Estoril | 05/01 12:00 | 25 | [207] Joao Domingues v Bolelli, Simone [153] | 3-6,2-6 | |
| ATP Estoril Qual | 04/30 12:35 | 45 | [153] Bolelli, Simone v Jaume Munar [161] | 6-1,6-4 | |
| ATP Estoril Qual | 04/29 15:25 | 44 | [155] Bolelli, Simone v Felix Auger Aliassime [186] | 6-4,6-1 | |
| Challenger - Barletta | 04/15 09:00 | 29 | [237] Marco Trungelliti v Bolelli, Simone [163] | 2-6,7-6,6-4 | |
| Challenger - Barletta | 04/14 13:35 | 28 | [406] Gian Marco Moroni v Bolelli, Simone [163] | 4-6,2-6 | |
| Challenger - Barletta | 04/13 12:30 | 27 | [163] Bolelli, Simone v Galovic, Viktor [194] | Retired | |
| Challenger - Barletta | 04/12 11:35 | 26 | [159] Lorenzo Sonego v Bolelli, Simone [163] | 5-7,3-6 | |
| Challenger - Barletta | 04/10 15:50 | 25 | [136] Oscar Otte v Bolelli, Simone [163] | 7-6,4-6,1-6 | |
| Marbella, Spain | 03/29 09:00 | 27 | [165] Bolelli, Simone v Guido Andreozzi [198] | 6-3,0-6,3-6 | |
| Marbella, Spain | 03/28 12:35 | 26 | [165] Bolelli, Simone v Jozef Kovalik [141] | 2-6,6-4,6-4 | |
| Marbella, Spain | 03/27 12:30 | 25 | [121] Martin, Andrej v Bolelli, Simone [165] | 6-1,0-6,1-6 | |
| Challenger - Santiago | 03/06 15:35 | 25 | Bolelli, Simone v Marco Cecchinato | 3-6,5-7 | |
| Challenger - Punta del Este | 03/03 23:00 | 29 | Bolelli, Simone v Guido Andreozzi | 6-3,4-6,3-6 | |
| Challenger - Punta del Este | 03/02 21:00 | 28 | Bolelli, Simone v Alessandro Giannessi | 6-2,7-5 | |
| Challenger - Punta del Este | 03/01 23:05 | 27 | Federico Gaio v Bolelli, Simone | 3-6,3-6 | |
| Challenger - Punta del Este | 02/28 18:30 | 26 | Gian Marco Moroni v Bolelli, Simone | 0-6,4-6 | |
| Challenger - Punta del Este | 02/27 21:00 | 25 | Maresca, Santiago v Bolelli, Simone | 2-6,1-6 | |
| Challenger Rennes | 01/24 20:00 | 26 | Bolelli, Simone v Ricardas Berankis | 5-7,3-6 | |
| Challenger Rennes | 01/22 13:25 | 25 | Bolelli, Simone v Sebastian Ofner | 6-2,7-6 | |
| Challenger Eckental | 11/02 17:30 | 26 | [175] Bolelli, Simone v Maximilian Marterer [106] | 7-6,6-7,3-6 | |
| Challenger Eckental | 10/31 13:45 | 25 | [447] Kern, Robin v Bolelli, Simone [175] | 6-7,2-6 | |
| ATP Vienna Qual | 10/22 12:00 | 46 | Bolelli, Simone v Herbert, Pierre-Hugues | 6-7,2-6 | |
| ATP Vienna Qual | 10/21 09:00 | 45 | [70] Dusan Lajovic v Bolelli, Simone [190] | 3-6,4-6 | |
| ATP Stockholm | 10/18 13:40 | 25 | [48] Troicki, Viktor v Bolelli, Simone [190] | 6-3,6-3 | |
| ATP Stockholm Qual | 10/16 11:15 | - | [190] Bolelli, Simone v Illya Marchenko [199] | 6-3,1-6,7-6 | |
| ATP Stockholm Qual | 10/15 13:30 | 26 | [137] Casper Ruud v Bolelli, Simone [196] | 4-6,4-6 | |
| Metz, France | 09/19 12:00 | 25 | [204] Bolelli, Simone v Granollers, Marcel [135] | 6-7,6-3,6-7 | |
| ATP Metz Qual | 09/18 11:00 | 46 | Ugo Humbert v Bolelli, Simone | 6-3,6-7,6-7 | |
| ATP Metz Qual | 09/17 11:10 | 45 | [204] Bolelli, Simone v Kamke, Tobias [182] | 7-6,6-3 | |
| Istanbul, Turkey | 09/13 13:00 | 26 | [101] Alexander Bublik v Bolelli, Simone [204] | 2-6,6-0,6-1 |