| ITF Italy F29 | 09/24 14:20 | 25 | [437] Stefanini, Jacopo v Varillas, Juan Pablo [346] | 3-6,4-6 | |
| Genoa, Italy | 09/02 17:20 | 46 | [442] Stefanini, Jacopo v Varillas, Juan Pablo [327] | 1-6,0-6 | |
| Genoa, Italy | 09/02 08:30 | 45 | Stefanini, Jacopo v Bottino, Edoardo | 6-1,3-6,6-3 | |
| ITF Italy F25 | 08/29 16:30 | 26 | Laurent Lokoli v Stefanini, Jacopo | 7-6,7-5 | |
| ITF Italy F25 | 08/27 13:15 | 25 | Stefanini, Jacopo v Borella, Filippo | 7-5,6-4 | |
| ITF Italy F15 | 06/20 12:10 | 25 | Stefanini, Jacopo v Lorenzo Bocchi | Walkover | |
| ITF Italy F14 | 06/12 11:10 | 25 | [419] Ornago, Fabrizio v Stefanini, Jacopo [417] | Retired | |
| ITF Italy F14 Qual | 06/10 08:30 | 54 | Stefanini, Jacopo v Coppini, Alessandro | 6-1,6-1 | |
| ITF Italy F14 Qual | 06/09 08:50 | 54 | Stefanini, Jacopo v Gabriele Moghini | 6-3,7-5 | |
| ITF Italy F13 | 06/06 09:55 | 26 | [283] Viola, Matteo v Stefanini, Jacopo [419] | 3-6,6-1,7-6 | |
| ITF Italy F13 | 06/04 11:00 | 25 | Stefanini, Jacopo v Marvin Moeller | 4-6,7-6,6-4 | |
| ITF Italy F12 | 05/30 10:30 | 26 | [419] Stefanini, Jacopo v Marcora, Roberto [476] | 6-7,1-6 | |
| ITF Italy F12 | 05/28 14:50 | 25 | Stefanini, Jacopo v Matthew Dellavedova | 6-1,6-2 | |
| ITF Italy F12 | 05/27 08:30 | 54 | Stefanini, Jacopo v Lorenzo Bocchi | 6-3,6-4 | |
| ITF Italy F12 | 05/26 08:00 | 54 | Stefanini, Jacopo v Virgili, Augusto | 6-2,6-2 | |
| Challenger Mestre Qual | 05/19 14:40 | 45 | [448] Stefanini, Jacopo v Kimmer Coppejans [362] | 6-4,3-6,0-6 | |
| ITF Italy F9 | 05/14 15:30 | 25 | Stefanini, Jacopo v Jannik Sinner | 3-6,1-6 | |
| Turkey F16, Singles Qualifying | 04/23 07:30 | 62 | Stefanini, Jacopo v Cutuli, Domenico | 6-1,3-6,4-6 | |
| Turkey F16, Singles Qualifying | 04/22 07:30 | 62 | Stefanini, Jacopo v Baryshev, Alexey | 6-1,6-2 | |
| Turkey F16, Singles Qualifying | 04/21 07:30 | 62 | Stefanini, Jacopo v Robin Thour | 6-4,6-3 | |
| Turkey F15, Singles Qualifying | 04/18 09:50 | 25 | Nerman Fatic v Stefanini, Jacopo | 7-5,6-4 | |
| ITF Tunisia F12 | 03/29 12:15 | 26 | Stefanini, Jacopo v Orlando Luz | 6-0,1-6,0-6 | |
| ITF Tunisia F12 | 03/28 10:05 | 25 | Stefanini, Jacopo v Makiguchi, Ryusei | 6-1,2-6,6-4 | |
| ITF Croatia F3 | 03/20 13:20 | 25 | [470] Stefanini, Jacopo v Geoffrey Blancaneaux [276] | 6-3,6-7,4-6 | |
| Tunisia F10, Singles Qualifying | 03/14 12:45 | 25 | Stefanini, Jacopo v Mariano Kestelboim | 4-6,0-6 | |
| ITF Spain F2 | 01/26 13:00 | 27 | Munoz-De la Nava, Daniel v Stefanini, Jacopo | 6-3,7-6 | |
| ITF Spain F2 | 01/24 09:00 | 26 | Stefanini, Jacopo v Billy Harris | 6-1,6-0 | |
| ITF Spain F2 | 01/22 09:00 | 25 | Hersey, Jake v Stefanini, Jacopo | 1-6,0-6 | |
| ITF Italy F34 | 10/17 15:05 | 25 | Stefanini, Jacopo v Giacalone, Omar | 3-6,4-6 | |
| ITF Italy F33 | 10/11 15:10 | 26 | Corentin Moutet v Stefanini, Jacopo | 6-3,6-1 |