2019 | Christopher Zablocki | M | 2:34:41 | Downtown/Munroe Street w/finish at Madison Social | 155 | Sheryl Rosen |
| Tamara Kozulina | F | 3:04:00 | | | |
2018 | Bryan Morseman | M | 2:26:56 | Downtown/Monroe Street, with finish at Kleman Plaza | 153 | Sheryl Rosen |
| Tamara Kozulina | F | 3:03:10 | | | |
2017 | Bryan Morseman | M | 2:27:12 | Downtown/Monroe Street | 180 | Ely Rosario |
| Tamara Kozulina | F | 3:09:25 | | | |
2016 | Kennedy Kemei | M | 2:31:34 | Downtown/Monroe Street | 224 | Ely Rosario & Eric Godin |
| Tamara Kozulina | F | 3:03:20 | | | |
2015 | Mark Chepses | M | 2:19:12 | | 335 | Jay Silvanima & Nancy Stedman |
| Sarah Crouch | F | 2:46:59 | | | |
2014 | Bryan Morseman | M | 2:24:29 | FSU/St. Marks Trail | 361 | Jay Silvanima & Nancy Stedman |
| Esther Erb | F | 2:46:29 | | | |
2013 | Chris Zablocki | M | 2:23:26 | FSU/St. Marks Trail | 307 | Jay Silvanima & Nancy Stedman |
| Nina Kraft | F | 2:52:49 | | | |
2012 | Solomon Kandie | M | 2:27:23 | FSU/St. Marks Trail | 270 | Jay Silvanima & Nancy Stedman |
| Leah Thorvilson | F | 2:40:06 | | | |
2011 | Esteban Vanegas | M | 2:28:38 | FSU/St. Marks Trail/Southwood | 234 | Jay Silvanima & Nancy Stedman |
| Karen Harvey | F | 2:43:32 | | | |
2010 | James Kiptoo | M | 2:26:49 | FSU/St. Marks Trail | 233 | Jay Silvanima & Nancy Stedman |
| Beth Moras | F | 3:16:05 | | | |
2009 | George Towett | M | 2:20:29 | FSU/St. Marks Trail | 203 | Jay Silvanima & Nancy Stedman |
| Nina Kraft | F | 2:45:05 | | | |
2008 | Scot Mullins | M | 2:24:01 | FSU/St. Marks Trail | 209 | Jay Silvanima |
| Tamara Kozulina | F | 3:03:38 | | | |
2007 | Judson Cake | M | 2:28:15 | FSU/St. Marks Trail | 168 | Jay Silvanima |
| Valerie Gortmaker | F | 2:46:09 | | | |
2006 | Michael Douma | M | 2:51:58 | FSU/St. Marks Trail | 79 | Jack McDermott |
| Teresa Lafleur | F | 3:32:11 | | | |
2005 | Jeff Dobias | M | 2:43:38 | FSU/St. Marks Trail | 129 | Jack McDermott & Toma Wilkerson |
| Lisa Purul | F | 3:24:24 | | | |
2004 | Jack McDermott | M | 2:55:19 | FSU/St. Marks Trail | 75 | Gary & Peg Griffin |
| Kim Bruce | F | 3:18:18 | | | |
2003 | Michael Western | M | 2:50:32 | Wakulla Springs | 38 | Gary & Peg Griffin |
| Kathy Pike | F | 3:34:48 | | | |
2002 | Ronnie Godwin & Felton Wright | M | 3:02:32 | Tallahassee Nurseries | 62 | Gary & Peg Griffin |
| Carrie Weyant | F | 3:21:17 | | | |
2001 | David Yon | M | 2:57:24 | Tallahassee Nurseries | 86 | Gary & Peg Griffin |
| Carrie Weyant | F | 3:36:01 | | | |
2000 | Michael Peck | M | 2:46:53 | Tallahassee Nurseries | 51 | Gary & Peg Griffin; Dana & Susan Stetson |
| Melissa Knechtel | F | 3:16:13 | | | |
1999 | Tom Minor | M | 2:56:17 | Education Building | 80 | Dana & Susan Stetson; Gary & Peg Grffin; Fred & Margarete Deckert |
| Martha Vidal | F | 3:13:51 | | | |
1998 | Bryon Law | M | 2:29:02 | Education Building | 73 | Dana Stetson & Fred Deckert |
| Carrie Weyant | F | 3:09:08 | | | |
1997 | Daniel Widener | M | 2:50:45 | Wacissa Springs | 111 | Dana Stetson & Kim Ortloff |
| Dee Farnell | F | 3:33:22 | | | |
1996 | William Flynn | M | 2:43:24 | Wacissa Springs | 70 | Dana Stetson |
| Krista Prentice | F | 3:29:44 | | | |
1995 | Paul Hough | M | 2:43:45 | Wacissa Springs | 124 | Charlie Yates; Chris Teaf; Ray Hanlon |
| Paula Johnson | F | 3:10:56 | | | |
1994 | Louis Floyd | M | 2:32:27 | Wacissa Springs | 133 | Charlie Yates & Joe Dexter |
| Lori Karison | F | 3:2:21 | | | |
1993 | Louis Foyd | M | 2:27:20 | Wacissa Springs | 83 | Lloyd Cline & Joe Dexter |
| Fran Fidler | F | 2:56:22 | | | |
1992 | Jessie Close | M | 2:28:41 | Wacissa Springs | 115 | Chris Teaf |
| Paula Johnson | F | 3:04:52 | | | |
1991 | Steve Carney | M | 2:44:41 | Wacissa Springs | 118 | Chris Teaf |
| Paula Johnson | F | 2:56:10 | | | |
1990 | Jessie Close | M | 2:28:43 | Wacissa Springs | 107 | Chris Teaf |
| Claudia Kasen | F | 3:02:18 | | | |
1989 | TC Carroll | M | 2:38:28 | Wacissa Springs | 93 | Chris Teaf |
| Paula Johnson | F | 3:07:13 | | | |
1989 | Tom Swiersz | M | 2:31:39 | Wacissa Springs | 49 | Frank Nearhoof |
| Lana Hayden | F | 3:19:54 | | | |
1987 | Scott Hinkle | M | 2:40:09 | Wacissa Springs | 72 | Frank Nearhoof |
| Laura Meighan | F | 3:14:57 | | | |
1986 | Felton Wright | M | 2:40:57 | Wacissa Springs | 44 | Frank Nearhoof |
| Joyce Hodges | F | 3:37:35 | | | |
1985 | Felton Wright | M | 2:41:50 | Killearn Estates | 44 | Mike Eakin |
| Debbie Moore | F | 3:17:09 | | | |
1984 | Rick Miller | M | 2:35:00 | Killearn Estates | 49 | Steve Meade |
| Donna Glotzbach | F | 3:11:34 | | | |
1983 | Mike Patterson | M | 2:23:55 | Killearn Estates | 81 | Steve Meade |
| Christy Orthmann | F | 3:15:06 | | | |
1982 | Chris Lingle | M | 2:28:11 | Killearn Estates | 95 | Steve Meade |
| Marianne Crawford | F | 3:14:31 | | | |
1981 | Jim Dickson | M | 2:37:39 | Killearn Estates | 41 | |
| Linda Abele | F | 3:49:48 | | | |
1980 | Steve Figard | M | 2:35:32 | Killearn Estates | 71 | |
| Victoria Myers | F | 3:30:33 | | | |
1979 | Steve Figard | M | 2:45:37 | Killearn Estates | 54 | |
| Shirley Silsby | F | 3:03:16 | | | |
1978 | Tim Simpkins | M | 2:39:00 | Springhill Road | 19 | |
| Donna Glotzbach | F | 3:45:00 | | | |
1977 | Tim Simpkins | M | 2:35:59 | Silver Lake | 22 | |
| Betty Ely | F | 3:38:59 | | | |
1976 | John Hargreaves | M | 2:58:00 | Campbell Stadium | 7 | |
| N/A | F | | | | |
1975 | John Hargreaves | M | 3:00:07 | Natural Bridge | 2 | |
| N/A | F | | | | |