| Jude Cianciola (Sr.) | Heritage Days Classic | | 21 | 19:57.11 |
| Jude Cianciola (Sr.) | Hope Heritage Days Classic | | 21 | 19:57.11 |
| Jude Cianciola (Sr.) | Rick Weinheimer Cross Country Classic | | 88 | 20:22.10 |
| Jude Cianciola (Sr.) | Athletic Annex/Riverview Health Flashrock Invitational | | 66 | 20:32.76 |
| Kade Thomas (Sr.) | Heritage Days Classic | | 45 | 22:13.91 |
| Kade Thomas (Sr.) | Hope Heritage Days Classic | | 45 | 22:13.91 |
| Kade Thomas (Sr.) | Bethesda Christian School Meet | | 39 | 22:14.36 |
| Kade Thomas (Sr.) | Morristown Invitational | | 40 | 23:07.39 |
| Jude Cianciola (Sr.) | Small School Invite | HS Boys | 144 | 23:09.90 |
| Kade Thomas (Sr.) | Indiana Christian & Home School State Championship | | 65 | 23:50.17 |
| Kade Thomas (Sr.) | Rick Weinheimer Cross Country Classic | | 139 | 24:09.40 |
| Tyler Sipkema (Sr.) | Indiana Christian & Home School State Championship | | 73 | 24:27.34 |
| Tyler Sipkema (Sr.) | Bethesda Christian School Meet | | 46 | 24:35.25 |
| Kade Thomas (Sr.) | Athletic Annex/Riverview Health Flashrock Invitational | | 90 | 24:35.71 |
| Tyler Sipkema (Sr.) | Hope Heritage Days Classic | | 54 | 24:43.58 |
| Tyler Sipkema (Sr.) | Heritage Days Classic | | 54 | 24:43.58 |
| Kade Thomas (Sr.) | Small School Invite | HS Boys | 187 | 25:01.20 |
| Tyler Sipkema (Sr.) | Rick Weinheimer Cross Country Classic | | 151 | 26:14.60 |
| Tyler Sipkema (Sr.) | Athletic Annex/Riverview Health Flashrock Invitational | | 92 | 26:27.60 |
| Tyler Sipkema (Sr.) | Small School Invite | HS Boys | 235 | 29:14.10 |
