| Matthew Kallhoff (Jr.) | Filmore Central Invitational | Fillmore Central Invitational | 12 | 17:47.88 |
| Matthew Kallhoff (Jr.) | Johnson Country Central Invite | Boys Varsity | 13 | 18:08.40 |
| Matthew Kallhoff (Jr.) | Malcolm Invitational | Malcolm Invitational | 13 | 18:20.30 |
| Matthew Kallhoff (Jr.) | Yutan Invite | Yutan Invite | 7 | 18:42.90 |
| Matthew Kallhoff (Jr.) | Milford Invitational | Milford Invitational | 7 | 18:50.32 |
| Matthew Kallhoff (Jr.) | UNK Invitational | UNK Invitational | 16 | 19:11.59 |
| Tristan Vieselmeyer (Fr.) | Johnson Country Central Invite | Boys Varsity | 38 | 19:56.50 |
| Tristan Vieselmeyer (Fr.) | Filmore Central Invitational | Fillmore Central Invitational | 57 | 20:08.35 |
| Isaac Bolte (Sr.) | Filmore Central Invitational | Fillmore Central Invitational | 61 | 20:22.38 |
| Jacob Garrison (Fr.) | Filmore Central Invitational | Fillmore Central Invitational | 66 | 20:37.05 |
| Tristan Vieselmeyer (Fr.) | Malcolm Invitational | Malcolm Invitational | 59 | 20:39.65 |
| Jon Saathoff (Fr.) | Malcolm Invitational | Malcolm Invitational | 61 | 20:42.90 |
| Jon Saathoff (Fr.) | Yutan Invite | Yutan Invite | 35 | 20:53.70 |
| Isaac Bolte (Sr.) | Johnson Country Central Invite | Boys Varsity | 50 | 21:01.70 |
| Tristan Vieselmeyer (Fr.) | Yutan Invite | Yutan Invite | 41 | 21:14.70 |
| Isaac Bolte (Sr.) | Malcolm Invitational | Malcolm Invitational | 73 | 21:17.42 |
| Jacob Garrison (Fr.) | Malcolm Invitational | Malcolm Invitational | 74 | 21:20.12 |
| Tristan Vieselmeyer (Fr.) | Milford Invitational | Milford Invitational | 27 | 21:23.44 |
| Jacob Garrison (Fr.) | Johnson Country Central Invite | Boys Varsity | 53 | 21:25.90 |
| Jon Saathoff (Fr.) | Milford Invitational | Milford Invitational | 28 | 21:29.58 |
| Jacob Garrison (Fr.) | Yutan Invite | Yutan Invite | 48 | 21:37.80 |
| Isaac Bolte (Sr.) | UNK Invitational | UNK Invitational | 75 | 21:37.99 |
| Jon Saathoff (Fr.) | UNK Invitational | UNK Invitational | 78 | 21:51.67 |
| Isaac Bolte (Sr.) | Yutan Invite | Yutan Invite | 54 | 22:03.80 |
| Isaac Bolte (Sr.) | Milford Invitational | Milford Invitational | 32 | 22:09.11 |
| Michael Zavodny (Fr.) | Yutan Invite | Yutan Invite | 58 | 22:11.20 |
| Tristan Vieselmeyer (Fr.) | UNK Invitational | UNK Invitational | 94 | 22:29.14 |
| Jacob Garrison (Fr.) | Milford Invitational | Milford Invitational | 36 | 22:31.52 |
| Michael Zavodny (Fr.) | Malcolm Invitational | Malcolm Invitational | 83 | 22:45.10 |
| David Shafer (Fr.) | Johnson Country Central Invite | Boys Varsity | 60 | 22:54.70 |
| Michael Zavodny (Fr.) | Filmore Central Invitational | Fillmore Central Invitational | 88 | 22:55.63 |
| Jacob Garrison (Fr.) | UNK Invitational | UNK Invitational | 108 | 22:58.37 |
| Michael Zavodny (Fr.) | Milford Invitational | Milford Invitational | 37 | 23:07.08 |
| David Shafer (Fr.) | Filmore Central Invitational | Fillmore Central Invitational | 92 | 23:10.97 |
| Jacob Johanson (Fr.) | Johnson Country Central Invite | Boys Varsity | 62 | 24:03.30 |
| David Shafer (Fr.) | UNK Invitational | UNK Invitational | 132 | 24:10.63 |