| UTR Pro Tennis Series Florida | 01/14 14:00 | - | Matthew Segura v Drew Van Orderlain | 4-6,6-4,5-3 | |
| UTR Pro Tennis Series Florida | 01/11 18:30 | - | Nick Chappell v Drew Van Orderlain | 6-1,7-5 | |
| UTR Pro Tennis Series Florida | 01/10 16:30 | - | Anze Arh v Drew Van Orderlain | 6-1,3-6,0-3 | |
| ITF Canada F7 | 09/08 13:00 | 44 | Perry Gregg v Drew Van Orderlain | 6-3,6-4 | |
| ITF Canada F6 | 09/02 13:00 | 62 | Maxime Cressy v Drew Van Orderlain | 6-2,6-3 | |
| ITF Canada F6 | 09/01 15:00 | 62 | Sebastian Zapata v Drew Van Orderlain | 2-6,0-6 | |
| ITF USA F23 Qual | 08/13 15:45 | 62 | Drew Van Orderlain v Jason Seidman | 4-6,4-6 | |
| ITF USA F23 Qual | 08/12 14:00 | 62 | Sergio Luis H Ramirez v Drew Van Orderlain | 1-6,5-7 | |
| ITF Canada F5 Qual | 07/02 16:00 | 54 | Joshua Peck v Drew Van Orderlain | 6-2,6-3 | |
| ITF Canada F4 Qual | 06/24 17:00 | 44 | Justin Roberts v Drew Van Orderlain | 6-4,6-3 | |
| ITF USA F16 | 06/16 19:00 | 62 | John McNally v Drew Van Orderlain | 7-6,6-3 | |
| ITF USA F13 Qual | 06/11 18:05 | 62 | Brian Shi v Drew Van Orderlain | 6-3,6-2 | |
| ITF USA F13 Qual | 06/10 14:00 | 62 | Drew Van Orderlain v Jonathan Chang | 7-5,6-2 | |
| ITF USA F12 | 04/21 22:00 | 60 | Drew Van Orderlain v Hillel Rousseau | 2-6,3-6 | |
| ITF USA F11 | 04/13 14:30 | 60 | Ronald Hohmann v Drew Van Orderlain | 6-7,7-6,6-4 | |
| ITF Canada F2 Qual | 03/04 15:00 | 44 | Drew Van Orderlain v Skander Mansouri | 2-6,3-6 | |
| ITF Canada F2 Qual | 03/03 15:00 | 44 | Matthew Kandath v Drew Van Orderlain | 3-6,6-3,5-7 | |
| ITF Canada F1 Qual | 02/24 15:00 | 44 | Drew Van Orderlain v Nicholas Reyes | 2-6,6-7 | |
| ITF USA F6 | 01/28 13:30 | 60 | Drew Van Orderlain v Ricardo David Mayagoitia | 2-6,5-7 | |
| ITF USA F5 | 01/20 14:00 | 45 | Drew Van Orderlain v Vlad Andrei Dancu | 4-6,2-6 | |
| ITF USA F5 | 01/19 13:00 | 44 | Temur Ismailov v Drew Van Orderlain | 3-6,1-6 | |
| ITF Canada F8 Qual | 09/18 18:45 | 44 | Alafia Ayeni v Drew Van Orderlain | 6-3,3-6,6-3 | |
| ITF Canada F7 Qual | 09/09 17:00 | 44 | Francis Pare v Drew Van Orderlain | 7-6,6-2 | |
| ITF Canada F6 Qual | 09/02 17:30 | 44 | Aidan Talcott v Drew Van Orderlain | 6-4,2-6,6-4 | |
| ITF USA F20 | 06/18 16:00 | 62 | Mark Oljaca v Drew Van Orderlain | 6-1,6-4 | |
| ITF USA F18 | 06/10 15:00 | 62 | Samuel Monette v Drew Van Orderlain | 6-3,6-2 | |
| ITF USA F16 | 04/30 13:00 | 60 | Axel Geller v Drew Van Orderlain | 6-3,6-2 | |
| ITF USA F16 | 04/29 13:45 | 60 | Joel Vincent Link v Drew Van Orderlain | Retired | |
| ITF USA F15 | 04/21 13:00 | 60 | Patrick Davidson v Drew Van Orderlain | 6-2,7-6 | |
| ITF USA F14 | 04/15 15:00 | 60 | Drew Van Orderlain v Oliver Crawford | 1-6,2-6 |