Stadium: Court 3 Round: 54
| Challenger Gatineau Qual | 2018/07/15 19:00 | Patrick Kypson v Borna Gojo | 7-6,6-2 |
| Challenger Gatineau Qual | 2018/07/14 18:25 | Joris De Loore v Patrick Kypson | 7-6,5-7,4-6 |
| Challenger Winnipeg Qual | 2018/07/09 18:20 | Patrick Kypson v Marc-Andrea Huesler | 2-6,4-6 |
| Challenger Winnipeg Qual | 2018/07/08 21:20 | Makoto Ochi v Patrick Kypson | 5-7,3-6 |
| Challenger Winnipeg Qual | 2018/07/08 16:35 | Patrick Kypson v James Frawley | 6-0,6-3 |
| ATP Miami Qual | 2018/03/20 16:10 | Cameron Norrie v Patrick Kypson | 6-7,6-3,6-1 |
| ATP Miami Qual | 2018/03/19 18:20 | Patrick Kypson v Tim Smyczek | 6-4,6-3 |
| Challenger Irving | 2018/03/13 20:00 | Patrick Kypson v Bjorn Fratangelo | 6-7,0-6 |
| Challenger Gatineau Qual | 2018/07/15 16:40 | Jacob Grills v Makoto Ochi | 1-6,7-5,6-1 |
| Challenger Gatineau Qual | 2018/07/14 21:55 | Jacob Grills v Jumpei Yamasaki | 6-3,6-1 |
| Challenger Winnipeg Qual | 2018/07/08 23:15 | Jack Mingjie Lin v Jacob Grills | 6-4,6-0 |
| Challenger Winnipeg Qual | 2018/07/08 20:05 | Nicaise Muamba v Jacob Grills | 6-7,0-6 |
| ITF Canada F5 | 2018/07/07 18:50 | Jacob Grills v William Griffith | 6-2,4-6,4-6 |
| ITF Canada F5 | 2018/07/06 17:00 | Marc-Andrea Huesler v Jacob Grills | 6-3,0-6,5-7 |
| ITF Canada F5 | 2018/07/05 20:45 | Justin Boulais v Jacob Grills | 7-5,1-6,3-6 |
| ITF Canada F5 | 2018/07/03 16:00 | Herbert Jody Maginley v Jacob Grills | 6-7,2-6 |