Stadium: Hard Court 4 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Tallahassee | 2023/10/23 14:00 | Alvin N Tudorica v Matthias Uwe Kask | 7-6,7-5 |
| ITF M25 Osijek | 2022/05/16 08:00 | Matthias Uwe Kask v Dimitrije Zubac | 6-4,6-7,5-10 |
| ITF M15 Dubrovnik | 2022/04/05 07:55 | Matthias Uwe Kask v Matic Dimic | 3-6,2-6 |
| ITF M15 Dubrovnik | 2022/04/04 14:30 | Joao M Nusdeo v Matthias Uwe Kask | 1-6,2-6 |
| ITF M25 Opatija | 2022/03/23 08:50 | Matthias Uwe Kask v Tommaso Compagnucci | 6-7,6-3,3-6 |
| ITF M25 Opatija | 2022/03/22 08:55 | Matthias Uwe Kask v Filippo Giovannini | 6-2,6-4 |
| ITF M25 Opatija | 2022/03/21 13:40 | Lorenzo Favero v Matthias Uwe Kask | 4-6,4-6 |
| ITF M25 Porec | 2022/03/09 12:50 | Duje Kekez v Matthias Uwe Kask | 6-3,6-3 |
| Challenger Calgary | 2023/11/05 19:55 | Drew Van Orderlain v Ryan Seggerman | 4-6,4-6 |
| ITF M25 Edmonton | 2023/10/31 17:20 | Nicolas Kotzen v Drew Van Orderlain | 6-2,6-4 |
| ITF M25 Edmonton | 2023/10/30 18:55 | Drew Van Orderlain v Frederick McRae | 6-0,6-0 |
| ITF M25 Edmonton | 2023/10/29 18:10 | Drew Van Orderlain v Igor Danich | 4-6,6-3,10-3 |
| ITF M25 Saint-Augustin | 2023/10/25 18:25 | Drew Van Orderlain v Junghee You | 4-6,6-1,5-7 |
| ITF M25 Saint-Augustin | 2023/10/24 14:00 | Drew Van Orderlain v Henry Lieberman | 6-4,7-6 |
| ITF M25 Saint-Augustin | 2023/10/23 14:00 | Drew Van Orderlain v Tom Dynka | 6-0,6-0 |
| ITF M15 Morelia | 2023/10/18 19:00 | Felix Corwin v Drew Van Orderlain | 6-4,6-2 |