| ITF Italy F33 | 10/10 14:30 | 25 | Mattia Frinzi v Jacopo Stefanini | 6-4,2-6,2-6 | |
| ITF Italy F33 Qual | 10/09 13:00 | 44 | Jacopo Stefanini v Andrea Borroni | 6-4,6-3 | |
| ITF Italy F32 | 10/04 17:30 | 26 | Corentin Moutet v Jacopo Stefanini | 6-2,6-4 | |
| ITF Italy F32 | 10/03 11:20 | 25 | Jacopo Stefanini v Jakob Sude | 6-7,7-6,6-1 | |
| ITF Italy F31 | 09/27 13:00 | 26 | Miljan Zekic v Jacopo Stefanini | 6-3,7-6 | |
| ITF Italy F31 | 09/26 14:25 | 25 | Jacopo Stefanini v Florian Fallert | Retired | |
| ITF Italy F30 | 09/20 17:05 | 26 | Lorenzo Sonego v Jacopo Stefanini | 6-0,6-2 | |
| ITF Italy F30 | 09/19 13:00 | 25 | Tim Slager v Jacopo Stefanini | 0-6,0-6 | |
| ITF Italy F29 | 09/13 13:00 | 26 | [440] Jacopo Stefanini v Jay Clarke [306] | 3-6,6-7 | |
| ITF Italy F29 | 09/12 13:00 | 25 | Andres Gabriel Ciurletti v Jacopo Stefanini | Retired | |
| ITF Italy F28 | 09/08 16:00 | 28 | [368] Jacopo Stefanini v Adelchi Virgili [465] | 4-6,3-6 | |
| ITF Italy F28 | 09/07 12:00 | 27 | Roberto Marcora v Jacopo Stefanini | 4-6,5-7 | |
| ITF Italy F28 | 09/06 09:25 | 26 | Jacopo Stefanini v Kirill Kivattsev | 6-4,6-1 | |
| ITF Italy F28 | 09/04 13:10 | 25 | Manfred Fellin v Jacopo Stefanini | 1-6,0-6 | |
| ITF Italy F27 | 08/31 19:45 | 27 | Igor Smilansky v Jacopo Stefanini | 6-3,6-7,7-5 | |
| ITF Italy F27 | 08/30 13:40 | 26 | Jacopo Berrettini v Jacopo Stefanini | 2-6,4-6 | |
| ITF Italy F27 | 08/28 13:45 | 25 | Luca Giacomini v Jacopo Stefanini | 2-6,6-4,2-6 | |
| ITF Italy F25 | 08/07 17:20 | 25 | Jacopo Stefanini v Omar Giacalone | 3-6,1-6 | |
| ITF Italy F24 | 07/31 19:00 | 25 | [326] Jay Clarke v Jacopo Stefanini [395] | 6-4,7-6 | |
| ITF Italy F23 | 07/26 10:00 | 26 | Simone Roncalli v Jacopo Stefanini | 7-5,6-4 | |
| ITF Italy F23 | 07/24 11:00 | 25 | [382] Jacopo Stefanini v Tomas Lipovsek Puches [386] | 6-2,6-1 | |
| Challenger San Benedetto Qual | 07/15 14:45 | 45 | Daniele Capecchi v Jacopo Stefanini | 7-5,1-6,6-3 | |
| ITF Italy F21 | 07/11 15:10 | 25 | [279] Andrea Collarini v Jacopo Stefanini [422] | 6-0,6-2 | |
| ITF Italy F20 | 07/06 12:00 | 27 | [279] Andrea Collarini v Jacopo Stefanini [422] | 6-0,6-3 | |
| ITF Italy F20 | 07/05 09:30 | 26 | Jacopo Stefanini v Cristian Carli | 4-6,7-6,7-6 | |
| ITF Italy F20 | 07/03 08:30 | 25 | Matteo De Vincentis v Jacopo Stefanini | 3-6,0-6 | |
| ITF Italy F18 | 06/22 16:05 | 26 | Pietro Rondoni v Jacopo Stefanini | 6-3,6-4 | |
| ITF Italy F18 | 06/20 11:10 | 25 | Lorenzo Bocchi v Jacopo Stefanini | 4-6,3-6 | |
| ITF Italy F17 | 06/13 12:00 | 25 | [483] Orlando Luz v Jacopo Stefanini [418] | 6-7,6-3,6-4 | |
| ITF Italy F16 | 06/07 11:45 | 26 | [440] Jacopo Stefanini v Maverick Banes [378] | 2-6,3-6 |