| ITF W75 Rome (GA) | 01/30 14:55 | 54 | [408] Jessica Failla v Victoria Osuigwe [441] | 2-6,3-6 | |
| ITF W75 Rome (GA) | 01/29 14:50 | 54 | Jessica Failla v Cherysh Endurance Henry | 6-0,6-1 | |
| ITF W35 Le Gosier | 01/25 20:35 | 26 | [281] Maria Mateas v Jessica Failla [407] | 6-2,7-5 | |
| ITF W35 Le Gosier | 01/24 17:05 | 25 | Jessica Failla v Nehanda Thomias | 6-0,6-2 | |
| ITF W35 Petit-Bourg | 01/17 14:00 | 25 | [281] Maria Mateas v Jessica Failla [407] | 6-1,6-2 | |
| ITF W40 Veracruz | 11/28 16:00 | 25 | [445] Victoria Rodriguez v Jessica Failla [495] | 6-2,4-6,6-1 | |
| ITF W25 Austin | 11/14 19:55 | 25 | [485] Jessica Failla v Chloe Beck [412] | 4-6,3-6 | |
| ITF W100 Charleston | 11/07 15:45 | 54 | [399] Jessica Failla v Alexis Blokhina [473] | 6-7,1-6 | |
| ITF W100 Charleston | 11/06 16:05 | 54 | Jessica Failla v Dasha Plekhanova | 6-3,6-4 | |
| ITF W15 Norman | 11/04 15:00 | 26 | Jessica Failla v Qavia Lopez | Cancelled | |
| ITF W15 Norman | 11/03 16:40 | 27 | Jessica Failla v Maria Kononova | 6-7,2-6 | |
| ITF W15 Norman | 11/02 15:00 | 26 | Jessica Failla v Jada Robinson | 6-1,6-3 | |
| ITF W15 Norman | 10/31 18:15 | 25 | Jessica Failla v Tiziana Rossini | 6-1,6-2 | |
| ITF W80 Tyler | 10/27 00:25 | 26 | [445] Jessica Failla v Maria Kozyreva [171] | 4-6,6-2,10-12 | |
| ITF W80 Tyler | 10/24 22:35 | 25 | [330] Sophie Chang v Jessica Failla [445] | 3-6,3-6 | |
| WTA Guadalajara | 09/15 16:00 | 14 | [156] Ann Li v Jessica Failla [430] | 6-1,6-1 | |
| ITF W100 Granby | 07/20 17:00 | 26 | [92] Rebecca Marino v Jessica Failla [431] | 6-2,6-0 | |
| ITF W100 Granby | 07/19 14:00 | 25 | Eryn Cayetano v Jessica Failla | 0-6,0-6 | |
| ITF W60 Saskatoon | 07/13 16:00 | 26 | [418] Jessica Failla v Katarina Kozarov [377] | 6-7,5-7 | |
| ITF W60 Saskatoon | 07/12 16:00 | 25 | [117] Kimberly Birrell v Jessica Failla [418] | 6-4,2-6,1-6 | |
| ITF W60 Madrid | 06/17 10:05 | 28 | Marta Soriano Santiago v Jessica Failla | 3-6,6-1,7-5 | |
| ITF W60 Madrid | 06/16 08:15 | 27 | [455] Jessica Failla v Sakura Hosogi [253] | 6-4,4-6,6-4 | |
| ITF W60 Madrid | 06/15 09:30 | 26 | Jessica Failla v Kira Pavlova | 6-3,6-0 | |
| ITF W60 Madrid | 06/14 07:30 | 25 | [224] Arianne Hartono v Jessica Failla [455] | 6-7,5-7 | |
| ITF W60 Madrid | 06/13 08:55 | 24 | [455] Jessica Failla v Yasmine Mansouri [481] | 6-2,6-1 | |
| ITF W25 Madrid | 06/08 09:05 | 25 | [266] Alexandra Eala v Jessica Failla [464] | 6-3,7-6 | |
| ITF W25 Yecla | 05/31 08:00 | 25 | Jessica Failla v Nahia Berecoechea | 2-6,0-6 | |
| ITF W15 Malaga | 05/26 11:45 | 27 | Varvara Lepchenko v Jessica Failla | 7-6,6-3 | |
| ITF W15 Malaga | 05/25 09:55 | 26 | Marina Benito v Jessica Failla | 0-6,2-6 | |
| ITF W15 Malaga | 05/24 10:10 | 25 | Anna Kislyak v Jessica Failla | 0-6,2-6 |