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| Time | YR | Date | Location | |
| Aaron Sweemer | 16:43 | Junior | 1991 | Middletown |
| Joe Ledda | 16:16 | Junior | 11/4/1993 | Middletown |
| Justin Combs | 16:40 | Junior | 11/4/1993 | Middletown |
| Justin Combs | 16:59 | Senior | 9/27/1994 | TJ |
| Joe Ledda | 16:55 | Senior | 10/4/1994 | Home |
| Justin Combs | 16:56 | Senior | 10/4/1994 | Home |
| Joe Ledda | 16:43 | Senior | 10/15/1994 | Lancer |
| Joe Ledda | 16:54 | Senior | 10/22/1994 | Westminster |
| Joe Ledda | 16:13 | Senior | 11/3/1994 | Middletown |
| Justin Combs | 16:25 | Senior | 11/3/1994 | Middletown |
| Vince Novak | 16:56 | Senior | 11/3/1994 | Middletown |
| Carl Henn | 16:47 | Sophomore | 9/14/2002 | Boonsboro |
| Carl Henn | 16:57* | Junior | 10/30/2003 | Middletown |
| Carl Henn | 16:28 | Senior | 9/11/2004 | Boonsboro |
| Eric Liberatore | 16:32 | Freshmen | 9/11/2004 | Boonsboro |
| Frank Sisolak | 16:34 | Senior | 9/11/2004 | Boonsboro |
| Jim Ridder | 16:36 | Junior | 9/11/2004 | Boonsboro |
| Bryan Mull | 16:50 | Senior | 9/11/2004 | Boonsboro |
| Carl Henn | 16:29 | Senior | 10/1/2004 | Harford EC |
| Eric Liberatore | 16:44 | Freshmen | 10/1/2004 | Harford EC |
| Frank Sisolak | 16:47 | Senior | 10/1/2004 | Harford EC |
| Bryan Mull | 16:50 | Senior | 10/1/2004 | Harford EC |
| Walter Bender | 16:57 | Senior | 10/1/2004 | Harford EC |
| Carl Henn | 16:48 | Senior | 10/9/2004 | Lancer |
| Eric Liberatore | 16:49 | Freshmen | 10/9/2004 | Lancer |
| Frank Sisolak | 16:54 | Senior | 10/9/2004 | Lancer |
| Carl Henn | 16:36* | Senior | 11/4/2004 | Middletown |
| Eric Liberatore | 16:39* | Freshmen | 11/4/2004 | Middletown |
| Bryan Mull | 16:48* | Senior | 11/4/2004 | Middletown |
| Jim Ridder | 16:51* | Junior | 11/4/2004 | Middletown |
| Frank Sisolak | 16:59* | Senior | 11/4/2004 | Middletown |
| Jim Ridder | 16:59 | Senior | 9/10/2005 | Boonsboro |
| Jim Ridder | 16:24 | Senior | 10/21/2005 | Libertytown |
| Andrew Cross | 16:51 | Freshmen | 10/21/2005 | Libertytown |
| Jim Ridder | 16:16* | Senior | 11/3/2005 | Middletown |
| Andrew Cross | 16:35* | Freshmen | 11/3/2005 | Middletown |
| Eric Liberatore | 16:19* | Sophomore | 11/3/2005 | Middletown |
| Eric Liberatore | 16:48 | Junior | 9/6/2006 | Libertytown |
*The Middletown Course used from 2002 to the present time is 2.96 miles in length. Due to this, these times were converted to a 3.0 mile time for inclusion in the 16 minute club.
"I look back on my life like a good day's work; it is done, and I am satisfied with it." ~Grandma Moses