| Houston, USA | 11/10 16:35 | 45 | Eskeland, Jacob v Harrison Adams | 1-6,1-6 | |
| ITF USA F28 | 10/16 18:00 | 25 | Eskeland, Jacob v Bryde, Trent | 6-7,3-6 | |
| ITF USA F28 | 10/15 14:00 | 62 | Shabaz, Michael v Eskeland, Jacob | Walkover | |
| ITF USA F28 | 10/14 15:00 | 62 | Eskeland, Jacob v Smith, Barnaby | 6-4,6-4 | |
| ITF USA F28 | 10/13 15:00 | 62 | Ferreira Leite, Matheus v Eskeland, Jacob | 3-6,2-6 | |
| ITF USA F27 | 10/07 15:00 | 62 | Eskeland, Jacob v Shabaz, Michael | 6-7,1-6 | |
| ITF USA F27 | 10/06 15:00 | 62 | Adamson, Alec v Eskeland, Jacob | 4-6,3-6 | |
| ITF Finland F1 | 08/01 07:00 | 25 | Eskeland, Jacob v Jonathan Mridha | 2-6,1-6 | |
| ITF Finland F1 Qual | 07/30 10:45 | 54 | Tuomi, Verneri v Eskeland, Jacob | 3-6,1-6 | |
| ITF Finland F1 Qual | 07/29 09:30 | 54 | Eskeland, Jacob v Foley, Piers | 6-4,7-6 | |
| ITF Sweden F2 Qual | 05/13 08:15 | 54 | Eskeland, Jacob v Taylor, Sam | 6-7,2-6 | |
| ITF Portugal F3 Qual | 03/12 12:30 | 60 | Eskeland, Jacob v Almeida, Tiago | 5-7,2-6 | |
| ITF Norway F3 | 10/29 08:00 | 54 | Eskeland, Jacob v Ask, Fredrik | 6-7,3-6 | |
| ITF Norway F2 | 10/22 11:00 | 54 | Gorazd Srbljak v Eskeland, Jacob | 7-5,6-1 | |
| ITF Norway F1 | 10/17 14:55 | 25 | Lucas Miedler v Eskeland, Jacob | 6-3,6-3 | |
| ITF Sweden F5 Qual | 10/02 08:00 | 54 | Adrian Bodmer v Eskeland, Jacob | 6-3,6-3 | |
| ITF Sweden F5 | 10/01 09:30 | 54 | Frost, Linus v Eskeland, Jacob | Walkover | |
| ITF Sweden F4 Qual | 09/24 16:05 | 54 | Eero Vasa v Eskeland, Jacob | 6-4,6-3 | |
| ITF Norway F3 | 11/02 09:00 | 25 | Eskeland, Jacob v Soderlund, Carl | 6-7,0-6 | |
| ITF Norway F2 | 10/25 09:00 | 54 | Petersen, Bjoern v Eskeland, Jacob | 6-4,6-2 | |
| ITF Norway F2 | 10/24 08:00 | 54 | Nordby, Markus v Eskeland, Jacob | 3-6,2-6 | |
| ITF Norway F1 | 10/19 13:00 | 25 | Sabanov, Matej v Eskeland, Jacob | 6-4,6-3 | |
| ITF Sweden F4 Qual | 09/20 11:30 | 54 | Samuelsson, Eric v Eskeland, Jacob | 4-6,6-4,6-2 | |
| ITF Sweden F4 Qual | 09/19 13:30 | 54 | Eskeland, Jacob v Arvid Nordquist | 6-3,6-2 | |
| ITF Norway F2 | 11/03 08:00 | - | Lucas Renard v Eskeland, Jacob | 6-4,7-5 | |
| ITF Norway F1 | 10/25 12:30 | - | Eskeland, Jacob v Press, Frederik | 4-6,3-6 |