| Challenger Winnipeg | 07/10 15:00 | 24 | Sigouin, Benjamin v Gomez-Herrera, Carlos | 6-2,3-6,6-3 | |
| ITF M15 Cancun | 06/29 14:00 | 28 | Sigouin, Benjamin v Nick Chappell | 3-6,5-7 | |
| ITF M15 Cancun | 06/28 13:30 | 27 | Sigouin, Benjamin v Brymer, Gage | 6-2,6-3 | |
| ITF M15 Cancun | 06/27 13:30 | 26 | Sigouin, Benjamin v Hernandez Serrano, Juan Alejandro | 6-7,7-5,6-1 | |
| ITF M15 Cancun | 06/25 13:30 | 25 | Sigouin, Benjamin v Preston Brown | 7-5,6-0 | |
| Tulsa, Singles Main, M-ITF-USA-16A | 06/18 20:50 | 25 | [453] Alexander Ritschard v Sigouin, Benjamin [485] | 4-6,6-1,7-5 | |
| Vancouver, Canada | 08/15 02:00 | 25 | Vasek Pospisil v Sigouin, Benjamin | 7-6,3-6,6-3 | |
| ATP Toronto Qual | 08/04 20:40 | 45 | Sigouin, Benjamin v Elias Ymer | 5-7,3-6 | |
| Challenger Granby | 07/24 14:00 | 25 | Sigouin, Benjamin v Lucas Miedler | 3-6,6-2,4-6 | |
| Gatineau, Canada | 07/19 16:35 | 26 | Ugo Humbert v Sigouin, Benjamin | 6-4,6-4 | |
| Gatineau, Canada | 07/17 17:45 | 25 | Sigouin, Benjamin v Liam Broady | 6-4,6-2 | |
| Challenger Winnipeg | 07/11 16:25 | 25 | Sigouin, Benjamin v Filip Peliwo | 6-0,4-6,3-6 | |
| ITF Canada F5 | 07/04 22:00 | 25 | Sigouin, Benjamin v Fawcett, Tom | Retired | |
| ITF Canada F4 | 06/30 20:00 | 28 | Aragone, JC v Sigouin, Benjamin | 6-1,6-7,6-4 | |
| ITF Canada F4 | 06/29 17:00 | 27 | Sigouin, Benjamin v Colin Markes | 6-2,7-6 | |
| ITF Canada F4 | 06/28 20:35 | 26 | Sigouin, Benjamin v Ortiz, Adrian | Retired | |
| ITF Canada F4 | 06/27 18:10 | 25 | Monette, Samuel v Sigouin, Benjamin | Retired | |
| ITF Canada F3 | 06/21 17:55 | 26 | Sigouin, Benjamin v Lu, Tyler | 6-7,3-6 | |
| ITF Canada F3 | 06/20 17:25 | 25 | Sigouin, Benjamin v Baadi, Taha | 6-0,6-1 | |
| Drummondville, Canada | 03/13 18:00 | 25 | Sigouin, Benjamin v Scholtz, Nicolaas | 1-6,6-2,4-6 | |
| ITF USA F40 | 12/07 18:00 | 26 | Sigouin, Benjamin v Moraing, Mats | 3-6,6-7 | |
| ITF USA F40 | 12/05 16:00 | 25 | E Gracia, Jose v Sigouin, Benjamin | 3-6,1-6 | |
| ITF USA F39 | 11/29 17:25 | 26 | Corrie, Edward v Sigouin, Benjamin | 6-3,6-3 | |
| ITF USA F39 | 11/27 21:05 | 25 | Baughman, Deiton v Sigouin, Benjamin | 2-6,6-7 | |
| ITF Canada F8 | 09/22 19:50 | 27 | Sigouin, Benjamin v Harrison Adams | 7-6,6-7,2-6 | |
| ITF Canada F8 | 09/21 18:10 | 26 | El Midhawy, Adam v Sigouin, Benjamin | 7-6,4-6,4-6 | |
| ITF Canada F8 | 09/20 15:10 | 25 | Krustev, Victor v Sigouin, Benjamin | 3-6,1-6 | |
| Canada F7, Singles | 09/15 15:00 | 28 | Nevolo, Dennis v Sigouin, Benjamin | 6-2,6-4 | |
| Canada F7, Singles | 09/14 14:00 | 27 | Halebian, Alexios v Sigouin, Benjamin | 3-6,3-6 | |
| Canada F7, Singles | 09/13 14:00 | 26 | Sigouin, Benjamin v Kobelt, Peter | 7-5,6-0 |