| Challenger Forli | 02/26 13:05 | 28 | [237] Mirza Basic v Jack Draper [162] | 2-6,7-6,4-6 | |
| Challenger Forli | 02/25 11:10 | 27 | [271] Michael Mmoh v Jack Draper [162] | 7-5,4-6,2-6 | |
| Challenger Forli | 02/24 11:50 | 26 | Jack Draper v Gianmarco Ferrari | 6-2,6-4 | |
| Challenger Forli | 02/22 18:50 | 25 | [193] Jesper De Jong v Jack Draper [162] | 6-4,4-6,6-7 | |
| Challenger Forli | 02/20 17:00 | 29 | [201] Jack Draper v Tim Van Rijthoven [236] | 6-1,6-2 | |
| Challenger Forli | 02/19 15:00 | 28 | [201] Jack Draper v Yosuke Watanuki [291] | 6-3,4-6,6-3 | |
| Challenger Forli | 02/18 16:50 | 27 | [201] Jack Draper v Evan Furness [301] | 6-2,6-3 | |
| Challenger Forli | 02/16 14:55 | 26 | [137] Quentin Halys v Jack Draper [201] | 6-7,4-6 | |
| Challenger Forli | 02/15 10:40 | 25 | [201] Jack Draper v Mirza Basic [231] | 6-2,6-2 | |
| Challenger Cherbourg | 02/11 10:30 | 27 | [68] Benjamin Bonzi v Jack Draper [207] | 7-6,6-2 | |
| Challenger Cherbourg | 02/10 12:00 | 26 | [207] Jack Draper v Maximilian Marterer [210] | 6-4,6-2 | |
| Challenger Cherbourg | 02/08 10:00 | 25 | [162] Gregoire Barrere v Jack Draper [207] | 4-6,6-1,3-6 | |
| Challenger Forli | 01/19 10:05 | 25 | [213] Jack Draper v Borna Gojo [286] | 6-7,3-6 | |
| Challenger Forli | 01/16 17:00 | 29 | [262] Jack Draper v Jay Clarke [211] | 6-3,6-0 | |
| Challenger Forli | 01/15 14:00 | 28 | [277] Zsombor Piros v Jack Draper [262] | Retired | |
| Challenger Forli | 01/14 11:00 | 27 | [276] Alexander Ritschard v Jack Draper [262] | 6-3,5-7,3-6 | |
| Challenger Forli | 01/12 13:05 | 26 | [306] Luca Nardi v Jack Draper [262] | 0-6,1-6 | |
| Challenger Forli | 01/10 14:10 | 25 | [311] Roberto Quiroz v Jack Draper [262] | 1-6,4-6 | |
| Challenger Bari | 11/24 12:00 | 26 | [259] Jack Draper v Thomas Fabbiano [213] | 4-6,3-6 | |
| Challenger Bari | 11/22 10:35 | 25 | [299] Yannick Maden v Jack Draper [259] | 6-7,1-6 | |
| Challenger Helsinki | 11/16 12:45 | 25 | [261] Jack Draper v Julian Lenz [304] | 5-7,1-6 | |
| Challenger Ortisei | 11/13 11:25 | 28 | [125] Oscar Otte v Jack Draper [278] | 7-6,6-4 | |
| Challenger Ortisei | 11/12 11:45 | 27 | [278] Jack Draper v Federico Gaio [151] | 6-7,7-6,6-2 | |
| Challenger Ortisei | 11/10 12:10 | 26 | [278] Jack Draper v Lucas Miedler [297] | 6-4,7-6 | |
| Challenger Ortisei | 11/08 13:00 | 25 | [148] Emilio Gomez v Jack Draper [278] | 4-6,2-6 | |
| Challenger Eckental | 11/02 11:50 | 25 | [134] Tomas Machac v Jack Draper [277] | 7-6,4-6,6-4 | |
| Challenger Seville | 09/08 15:00 | 26 | [272] Jack Draper v Marcelo Tomas Barrios Vera [172] | Retired | |
| Challenger Seville | 09/07 09:00 | 25 | [316] Michael Geerts v Jack Draper [272] | 3-6,2-6 | |
| Challenger Como | 08/31 10:30 | 25 | [272] Jack Draper v Andrea Vavassori [358] | 4-6,6-2,3-6 | |
| Challenger Como | 08/31 08:00 | 25 | Jack Draper v Thiago Agustin Tirante | Cancelled |