| Michael Kennedy (Sr.) | Class 2A District 15 Championships | Varsity | 2 | 16:25.47 |
| Michael Kennedy (Sr.) | Class 2A State Championships | Varsity | 27 | 16:26.74 |
| Michael Kennedy (Sr.) | Spanish River Invitational | 1A/2A Varsity | 5 | 16:30.25 |
| Michael Cabral (Sr.) | Class 2A State Championships | Varsity | 29 | 16:30.67 |
| Matthew Stein (Sr.) | Class 2A State Championships | Varsity | 36 | 16:36.02 |
| Michael Kennedy (Sr.) | Class 2A Region 4 Championships | Varsity | 10 | 16:44.02 |
| Michael Cabral (Sr.) | Class 2A District 15 Championships | Varsity | 4 | 16:47.35 |
| Matthew Stein (Sr.) | Class 2A District 15 Championships | Varsity | 5 | 16:52.57 |
| Michael Kennedy (Sr.) | Pine Crest Invitational | Varsity | 3 | 16:53.83 |
| Michael Cabral (Sr.) | Class 2A Region 4 Championships | Varsity | 12 | 16:56.44 |
| Matthew Stein (Sr.) | Class 2A Region 4 Championships | Varsity | 15 | 17:02.34 |
| Michael Cabral (Sr.) | Spanish River Invitational | 1A/2A Varsity | 7 | 17:06.12 |
| Michael Cabral (Sr.) | Pine Crest Invitational | Varsity | 4 | 17:06.64 |
| Michael Kennedy (Sr.) | King of the Hill Invitational | Varsity | 8 | 17:09.23 |
| Ron Knezevich (Sr.) | Class 2A State Championships | Varsity | 66 | 17:18.00 |
| Alec Gugel (Sr.) | Class 2A State Championships | Varsity | 68 | 17:21.00 |
| Alec Gugel (Sr.) | Class 2A District 15 Championships | Varsity | 7 | 17:21.81 |
| Ron Knezevich (Sr.) | Class 2A Region 4 Championships | Varsity | 20 | 17:22.45 |
| Adrian Abedon (So.) | Class 2A State Championships | Varsity | 70 | 17:22.76 |
| Matthew Stein (Sr.) | Pine Crest Invitational | Varsity | 5 | 17:22.76 |
| Adrian Abedon (So.) | Class 2A District 15 Championships | Varsity | 8 | 17:23.84 |
| Michael Cabral (Sr.) | King of the Hill Invitational | Varsity | 14 | 17:24.35 |
| Ron Knezevich (Sr.) | Spanish River Invitational | 1A/2A Varsity | 11 | 17:28.65 |
| Ron Knezevich (Sr.) | Class 2A District 15 Championships | Varsity | 10 | 17:37.02 |
| Matthew Stein (Sr.) | Spanish River Invitational | 1A/2A Varsity | 16 | 17:39.24 |
| Alec Gugel (Sr.) | Spanish River Invitational | 1A/2A Varsity | 21 | 17:50.26 |
| Alec Gugel (Sr.) | Class 2A Region 4 Championships | Varsity | 36 | 17:59.36 |
| Alec Gugel (Sr.) | Pine Crest Invitational | Varsity | 10 | 18:01.83 |
| Matthew Stein (Sr.) | King of the Hill Invitational | Varsity | 28 | 18:05.54 |
| Adrian Abedon (So.) | Class 2A Region 4 Championships | Varsity | 39 | 18:08.65 |
| Gabriel Ortega (So.) | Class 2A District 15 Championships | Varsity | 13 | 18:11.71 |
| Ron Knezevich (Sr.) | Pine Crest Invitational | Varsity | 13 | 18:15.11 |
| Michael Kennedy (Sr.) | Estero DDD Invitational | Varsity | 5 | 18:18.00 |
| Alec Gugel (Sr.) | King of the Hill Invitational | Varsity | 33 | 18:18.92 |
| Matt Jordan (Jr.) | Class 2A District 15 Championships | Varsity | 18 | 18:26.67 |
| Adrian Abedon (So.) | Pine Crest Invitational | Varsity | 16 | 18:28.73 |
| Jabari Owens (So.) | Class 2A District 15 Championships | Varsity | 22 | 18:37.54 |
| Gabriel Ortega (So.) | Spanish River Invitational | 1A/2A Varsity | 32 | 18:38.72 |
| Adrian Abedon (So.) | Spanish River Invitational | 1A/2A Varsity | 33 | 18:39.05 |
| Adrian Abedon (So.) | King of the Hill Invitational | Varsity | 50 | 18:43.18 |
| Matthew Stein (Sr.) | Estero DDD Invitational | Varsity | 21 | 18:55.00 |
| Gabriel Ortega (So.) | King of the Hill Invitational | Varsity | 61 | 18:57.84 |
| Ron Knezevich (Sr.) | King of the Hill Invitational | Varsity | 68 | 19:03.75 |
| Ron Knezevich (Sr.) | Estero DDD Invitational | Varsity | 29 | 19:08.00 |
| Alec Gugel (Sr.) | Estero DDD Invitational | Varsity | 30 | 19:08.00 |
| Gabriel Ortega (So.) | Class 2A Region 4 Championships | Varsity | 83 | 19:33.74 |
| Matt Jordan (Jr.) | King of the Hill Invitational | Varsity | 99 | 19:43.91 |
| Jabari Owens (So.) | Pine Crest Invitational | JV | 1 | 19:44.44 |
| Riley Ward (Sr.) | Pine Crest Invitational | JV | 2 | 19:55.78 |
| Adrian Abedon (So.) | Estero DDD Invitational | Varsity | 55 | 19:59.00 |
| Jabari Owens (So.) | Spanish River Invitational | 1A/2A JV | 1 | 20:06.48 |
| Gabriel Ortega (So.) | Pine Crest Invitational | Varsity | 65 | 20:07.18 |
| Riley Ward (Sr.) | King of the Hill Invitational | Varsity | 124 | 20:13.60 |
| Ben Brody (Sr.) | Class 2A District 15 Championships | Varsity | 52 | 20:34.11 |
| Gabriel Ortega (So.) | Estero DDD Invitational | Varsity | 68 | 20:51.00 |
| Riley Ward (Sr.) | Spanish River Invitational | 1A/2A JV | 5 | 20:53.65 |
| Ben Brody (Sr.) | Pine Crest Invitational | JV | 7 | 21:06.54 |
| Ben Brody (Sr.) | Spanish River Invitational | 1A/2A JV | 11 | 21:33.33 |
| Ben Brody (Sr.) | King of the Hill Invitational | Varsity | 184 | 21:47.83 |
| Josh Koolik (Fr.) | Pine Crest Invitational | JV | 15 | 21:48.34 |
| Josh Koolik (Fr.) | King of the Hill Invitational | JV | 60 | 21:54.17 |
| Josh Koolik (Fr.) | Spanish River Invitational | 1A/2A JV | 27 | 22:22.83 |
| Sebastian Rukes (So.) | Pine Crest Invitational | JV | 22 | 22:33.75 |
| Jabari Owens (So.) | Estero DDD Invitational | JV | 31 | 22:38.00 |
| Ricky Morse (Jr.) | Pine Crest Invitational | JV | 24 | 22:43.46 |
| Ben Brody (Sr.) | Estero DDD Invitational | JV | 41 | 23:21.00 |
| Riley Ward (Sr.) | Estero DDD Invitational | JV | 42 | 23:29.00 |
| Jackson Ferrando (So.) | Pine Crest Invitational | JV | 31 | 23:36.43 |
| Andrew Asnis (So.) | Pine Crest Invitational | JV | 32 | 23:37.13 |
| Jack Rizzo (So.) | Estero DDD Invitational | JV | 46 | 23:41.00 |
| Josh Koolik (Fr.) | Estero DDD Invitational | JV | 58 | 24:06.00 |
| Sebastian Rukes (So.) | King of the Hill Invitational | JV | 130 | 24:13.23 |
| Ricky Morse (Jr.) | Spanish River Invitational | 1A/2A JV | 54 | 24:16.06 |
| Zachary Blostein (So.) | Pine Crest Invitational | JV | 51 | 26:23.04 |
| Ethan Leifert (Fr.) | King of the Hill Invitational | JV | 178 | 26:35.77 |
| Sebastian Rukes (So.) | Estero DDD Invitational | JV | 95 | 27:28.00 |
| Ethan Leifert (Fr.) | Estero DDD Invitational | JV | | 31:31.00 |
| Nikhil Narwani (Fr.) | Pine Crest Invitational | JV | 68 | 32:51.34 |
