| Date | Type | Name [last, first, grade] | School | Time | Avg/Mile |
| 10-27-2007 | County Championship Varsity Race | Dupont, Pat (12) | Fairport | 16:01 | 5:15.1 |
| 10-29-2005 | County Championship Varsity Race | Robinson, Corey (11) | Odyssey | 16:01.4 | 5:15.2 |
| 10-29-2005 | County Championship Varsity Race | Deady, Matt (12) | Fairport | 16:07.8 | 5:17.3 |
| 10-29-2005 | County Championship Varsity Race | Coon, Craig (12) | Penfield | 16:16.3 | 5:20.1 |
| 9-23-2008 | League Meet Race | Brimstein, Alex (12) | Thomas | 16:20 | 5:21.3 |
| 9-23-2008 | League Meet Race | Redfield, Greg (12) | Penfield | 16:23 | 5:22.3 |
| 10-27-2007 | County Championship Varsity Race | Stachecki, Tyler (12) | Penfield | 16:31 | 5:24.9 |
| 10-29-2005 | County Championship Varsity Race | Martina, Matt (12) | Penfield | 16:31.7 | 5:25.1 |
| 10-18-2011 | League Meet Race | Kozyra, Nate (12) | Rush Henrietta | 16:32 | 5:25.2 |
| 10-28-2006 | County Championship Varsity Race | Robinson, Corey (12) | Odyssey | 16:33.1 | 5:25.6 |
| 10-29-2005 | County Championship Varsity Race | English, Eric (11) | Mendon | 16:36.8 | 5:26.8 |
| 9-9-2008 | League Meet Race | Redfield, Greg (12) | Penfield | 16:36.8 | 5:26.8 |
| 9-19-2006 | League Meet Race | Robinson, Corey (12) | Odyssey | 16:37 | 5:26.9 |
| 10-29-2005 | County Championship Varsity Race | Dupont, Pat (10) | Fairport | 16:37.9 | 5:27.2 |
| 10-18-2011 | League Meet Race | Burke, Mickey (10) | Rush Henrietta | 16:38 | 5:27.2 |
| 10-29-2005 | County Championship Varsity Race | Bloom, Ryan (11) | Spencerport | 16:38.8 | 5:27.5 |
| 10-10-2006 | League Meet Race | Streb, Mark (12) | Brockport | 16:39 | 5:27.5 |
| 10-1-2013 | League Meet Race | Ronchetti, Will (12) | Brighton | 16:40 | 5:27.9 |
| 10-28-2006 | County Championship Varsity Race | Kaiser, Ryan (12) | Penfield | 16:41 | 5:28.2 |
| 10-25-2008 | County Championship Varsity Race | Redfield, Greg (12) | Penfield | 16:41 | 5:28.2 |
| 10-18-2011 | League Meet Race | Sweeney, Andrew (12) | Rush Henrietta | 16:41 | 5:28.2 |
| 10-29-2005 | County Championship Varsity Race | Phipps, Bill (12) | Sutherland | 16:41.2 | 5:28.3 |
| 10-28-2006 | County Championship Varsity Race | Dupont, Pat (11) | Fairport | 16:41.4 | 5:28.3 |
| 10-29-2005 | County Championship Varsity Race | Streb, Mark (11) | Brockport | 16:41.6 | 5:28.4 |
| 9-26-2006 | League Meet Race | Quinn, Tim (12) | Sutherland | 16:44 | 5:29.2 |