| Owen Rush (So.) | Morristown (IN) | | 3 | 18:28.00 |
| Owen Rush (So.) | Whiteland Invitational | Varsity Boys Race | 33 | 18:33.50 |
| Owen Rush (So.) | 2014 IHSAA Brown County Boys Cross Country Sectional Meet | | 38 | 18:36.04 |
| Owen Rush (So.) | Shelby County Invitational | | 6 | 18:41.10 |
| Owen Rush (So.) | Heritage Days Classic | | 8 | 18:50.00 |
| David Seelye (Fr.) | Heritage Days Classic | | 11 | 19:09.00 |
| Owen Rush (So.) | Greensburg Invitational | | 30 | 19:10.17 |
| Owen Rush (So.) | Mid-Hoosier Conference Meet | Event 4 Boys 5k Run CC | 20 | 19:16.00 |
| Owen Rush (So.) | Rushville Cross Country Classic | Event 2 Boys 5k Run Division III | 33 | 19:17.06 |
| Owen Rush (So.) | Edinburgh Triangular | | 1 | 19:23.00 |
| David Seelye (Fr.) | Morristown (IN) | | 5 | 19:31.00 |
| Dalton McKinney (Sr.) | Whiteland Invitational | Varsity Boys Race | 57 | 19:31.40 |
| David Seelye (Fr.) | Greensburg Invitational | | 39 | 19:32.79 |
| David Seelye (Fr.) | 2014 IHSAA Brown County Boys Cross Country Sectional Meet | | 53 | 19:37.53 |
| Dalton McKinney (Sr.) | Edinburgh Triangular | | 3 | 19:38.00 |
| David Seelye (Fr.) | Mid-Hoosier Conference Meet | Event 4 Boys 5k Run CC | 27 | 19:40.33 |
| David Seelye (Fr.) | Shelby County Invitational | | 15 | 19:48.90 |
| Dalton McKinney (Sr.) | Morristown (IN) | | 6 | 19:49.00 |
| David Seelye (Fr.) | Whiteland Invitational | Varsity Boys Race | 64 | 19:57.90 |
| Dalton McKinney (Sr.) | Shelby County Invitational | | 16 | 20:00.10 |
| Dalton McKinney (Sr.) | Greensburg Invitational | | 49 | 20:06.98 |
| David Seelye (Fr.) | Edinburgh Triangular | | 5 | 20:11.00 |
| Wyatt Whittington (Sr.) | Morristown (IN) | | 8 | 20:14.00 |
| Jordan Johnson (Fr.) | Morristown (IN) | | 7 | 20:14.00 |
| Jordan Johnson (Fr.) | Mid-Hoosier Conference Meet | Event 4 Boys 5k Run CC | 36 | 20:16.60 |
| Dalton McKinney (Sr.) | Heritage Days Classic | | 23 | 20:18.00 |
| Wyatt Whittington (Sr.) | Shelby County Invitational | | 20 | 20:25.50 |
| Dalton McKinney (Sr.) | 2014 IHSAA Brown County Boys Cross Country Sectional Meet | | 62 | 20:26.40 |
| David Seelye (Fr.) | Rushville Cross Country Classic | Event 2 Boys 5k Run Division III | 56 | 20:30.26 |
| Austin Everroad (So.) | Heritage Days Classic | | 25 | 20:35.00 |
| Jordan Johnson (Fr.) | Heritage Days Classic | | 26 | 20:36.00 |
| Josh Adams (Jr.) | Morristown (IN) | | 11 | 20:37.00 |
| Dalton McKinney (Sr.) | Mid-Hoosier Conference Meet | Event 4 Boys 5k Run CC | 43 | 20:43.50 |
| Wyatt Whittington (Sr.) | Whiteland Invitational | Varsity Boys Race | 74 | 20:46.10 |
| Austin Everroad (So.) | Morristown (IN) | | 12 | 20:49.00 |
| Jordan Johnson (Fr.) | 2014 IHSAA Brown County Boys Cross Country Sectional Meet | | 65 | 20:49.22 |
| Josh Adams (Jr.) | 2014 IHSAA Brown County Boys Cross Country Sectional Meet | | 66 | 20:55.31 |
| Wyatt Whittington (Sr.) | 2014 IHSAA Brown County Boys Cross Country Sectional Meet | | 68 | 20:58.72 |
| Josh Adams (Jr.) | Shelby County Invitational | | 28 | 21:00.20 |
| Austin Everroad (So.) | 2014 IHSAA Brown County Boys Cross Country Sectional Meet | | 70 | 21:06.71 |
| Josh Adams (Jr.) | Whiteland Invitational | Varsity Boys Race | 78 | 21:08.60 |
| Jordan Johnson (Fr.) | Shelby County Invitational | | 30 | 21:11.50 |
| Josh Adams (Jr.) | Greensburg Invitational | | 64 | 21:14.00 |
| Wyatt Whittington (Sr.) | Edinburgh Triangular | | 11 | 21:19.00 |
| Wyatt Whittington (Sr.) | Greensburg Invitational | | 65 | 21:21.29 |
| Austin Everroad (So.) | Mid-Hoosier Conference Meet | Event 4 Boys 5k Run CC | 48 | 21:25.83 |
| Austin Everroad (So.) | Greensburg Invitational | | 68 | 21:28.90 |
| Mauro Cumbe (Jr.) | Morristown (IN) | | 13 | 21:33.00 |
| Josh Adams (Jr.) | Mid-Hoosier Conference Meet | Event 4 Boys 5k Run CC | 49 | 21:33.65 |
| Jordan Johnson (Fr.) | Whiteland Invitational | Varsity Boys Race | 83 | 21:35.50 |
| Austin Everroad (So.) | Whiteland Invitational | Varsity Boys Race | 82 | 21:35.50 |
| Jordan Johnson (Fr.) | Greensburg Invitational | | 70 | 21:36.52 |
| Austin Everroad (So.) | Edinburgh Triangular | | 12 | 21:40.00 |
| Jordan Johnson (Fr.) | Edinburgh Triangular | | 13 | 21:43.00 |
| Josh Adams (Jr.) | Edinburgh Triangular | | 14 | 21:45.00 |
| Josh Adams (Jr.) | Heritage Days Classic | | 39 | 21:50.00 |
| Austin Everroad (So.) | Rushville Cross Country Classic | Event 2 Boys 5k Run Division III | 80 | 22:01.71 |
| Sam Robinson (Fr.) | Heritage Days Classic | | 41 | 22:09.00 |
| Sam Robinson (Fr.) | Whiteland Invitational | Boys JV Race | 31 | 22:10.00 |
| Mauro Cumbe (Jr.) | Shelby County Invitational | | 35 | 22:10.70 |
| Mauro Cumbe (Jr.) | Edinburgh Triangular | | 16 | 22:25.00 |
| Wyatt Whittington (Sr.) | Rushville Cross Country Classic | Event 2 Boys 5k Run Division III | 86 | 22:26.59 |
| Josh Adams (Jr.) | Rushville Cross Country Classic | Event 2 Boys 5k Run Division III | 88 | 22:48.48 |
| Taylor Benge (Fr.) | Shelby County Invitational | | 38 | 22:50.20 |
| Sam Robinson (Fr.) | Shelby County Invitational | | 40 | 22:54.10 |
| Wyatt Whittington (Sr.) | Heritage Days Classic | | 42 | 22:55.00 |
| Sam Robinson (Fr.) | Edinburgh Triangular | | 18 | 23:12.00 |
| Sam Robinson (Fr.) | Rushville Cross Country Classic | Event 2 Boys 5k Run Division III | 92 | 23:31.39 |
| Taylor Benge (Fr.) | Whiteland Invitational | Boys JV Race | 41 | 24:12.00 |
| Taylor Benge (Fr.) | Morristown (IN) | | 14 | 24:20.00 |
| Hunter Albright (So.) | Morristown (IN) | | 16 | 24:45.00 |
| Taylor Benge (Fr.) | Heritage Days Classic | | 49 | 24:54.00 |
| Hunter Albright (So.) | Heritage Days Classic | | 50 | 25:02.00 |
| Hunter Albright (So.) | Shelby County Invitational | | 52 | 27:23.50 |
| Taylor Benge (Fr.) | Edinburgh Triangular | | 20 | 28:31.00 |
