| Year | Division | Runner | School | Time | Team Winner | Points |
| 2025 | Varsity Boys | Tristan Kujawa | SLUH | 16:49.4 | SLUH | 16 |
| Varsity Girls | Grace Murphy | Nerinx Hall | 19:28.1 | St. Joseph’s Academy | 57 | |
| JV Boys (Large) | Edmund Reske | SLUH | 17:24.4 | SLUH | 15 | |
| JV Boys (Small) | Noah Aldridge | Priory | 18.25.0 | Priory | 67 |
**JV Girls races cancelled due to inclement weather**
| 2024 | Varsity Boys | Jacob Fitzpatrick | SLUH | 16:45.1 | SLUH | 16pts |
| JV Boys (Large) | Jaden Elgin | SLUH | 17:14.6 | SLUH | 15pts | |
| JV Boys (Small) | Ben Mattull | Providence | 19:58.6 | Lutheran South | 36pts | |
| Varsity Girls | Sydney Krus | Nerinx Hall | 19:27.7 | Nerinx Hall | 46ts | |
| JV Girls (Large) | Sadie Neff | St. Joseph’s | 22:25.8 | St. Joseph’s | 25pts | |
| JV Girls (Small) | Sonya Myskowski | Blue Knights | 23:32.0 | Blue Knights | 24pts |
| 2023 | Varsity Boys | George Donahue | SLUH | 16:33.2 | SLUH | 17pts |
| JV Boys (Large) | Matthew Musial | SLUH | 17:07.2 | SLUH | 15pts | |
| JV Boys (Small) | Jack Mahoney | Lutheran (St. Charles) | 18:30.1 | Lutheran South | 56pts | |
| Varsity Girls | Savannah Amann | St. Joseph’s Academy | 19:15.0 | St. Joseph’s Academy | 39pts | |
| JV Girls (Large) | Sadie Neff | St. Joseph’s Academy | 22:25.5 | St. Joseph’s Academy | 19pts | |
| JV Girls (Small) | Lynn Criswell | St. Louis Blue Knights | 22:41.7 | St. Louis Blue Knights | 23pts |
| 2022 | Varsity Boys | Adam Snoke | Lutheran South | 16:00.8 | SLUH | 33pts |
| JV Boys (Large) | Matthew Musial | SLUH | 17:58.0 | SLUH | 15pts | |
| JV Boys (Small) | Evan Hugge | Priory | 18:39.0 | Priory | 41pts | |
| Varsity Girls | Kensington Curd | Brentwood | 20:03.5 | St. Joseph’s Academy | 43pts | |
| JV Girls (Large) | Bailey Bryan | St. Joseph’s Academy | 22.06.8 | St. Joseph’s Academy | 25pts | |
| JV Girls (Small) | Amelia Smith | Collegiate School | 23:38.8 | Lutheran South | 41pts |
| 2021 | Varsity Boys | Caleb Lind | Lutheran St. Charles | 15:44.9 | SLUH | 55pts |
| JV Boys (Large) | Mason Scargall | SLUH | 17:14.1 | SLUH | 15pts | |
| JV Boys (Small) | Yuri Batan | Priory | 18:30.0 | Priory | 30pts | |
| Varsity Girls | Grace Schaff | Lutheran St. Charles | 19:51.5 | John Burroughs | 84pts | |
| JV Girls (Large) | Lillian Busby | St. Dominic | 22.05.6 | St. Dominic | 21pts | |
| JV Girls (Small) | Tabitha Bryant | St. Louis Blue Knights | 22.30.9 | St. Louis Blue Knights | 17pts |
| 2020 | Boys | Colin Ring | Westminster Christian | 16:55.9 | ||
| Girls | Macy Schelp | Lutheran South | 20:16.6 |
| 2019 | Varsity Boys | Malik Stewart | Maplewood | 16:39.6 | Parkway West | 64pts |
| JV Boys | Grant Patten | Parkway West | 19:30.8 | Parkway West | 17pts | |
| Varsity Girls | Tabitha Bevan | Parkway North | 20:10.8 | Parkway North | 44pts | |
| JV Girls | Selah Sparks | Providence Classical | 24:23.0 | Pattonville | 27pts |
| Year | Division | Runner | School | Winning Time | Team Winner | Team Points |
| 2018 | Boys Barker | Marquist Hutchinson | Cleveland NJROTC | 17:30.98 | Steelville | 37pts |
| Boys Hartmann | Will Green | Pacific | 17:00.50 | Westminster | 40pts | |
| Boys Borsa | Cody Poskin | Northwest | 17:09.48 | Parkway South | 25pts | |
| Girls Barker | Jordan Heacock | Jefferson (Festus) | 21.:01.88 | Jefferson (Festus) | 26pts | |
| Girls Hartmann | Macy Schelp | Lutheran South | 20:11.06 | Westminster | 42pts | |
| Girls Borsa | Tabitha Bevan | Parkway North | 19:41.35 | Washington | 15pts |
| 2017 | Boys Barker | Malik Stewart | Maplewood | 17:43.7 | New Haven | 47pts |
| Boys Hartmann | Alex Dukes | Mexico | 16:47.2 | Pleasant Hill | 81pts | |
| Boys Borsa | Maxwell McDaniel | Festus | 16:18.7 | West Plains | 30pts | |
| Girls Barker | Jordan Heacock | Jefferson (Festus) | 21:48.8 | Father Tolton | 31pts | |
| Girls Hartmann | Sarah Moore | Ste. Genevieve | 20:17.6 | Helias Catholic | 66pts | |
| Girls Borsa | Kaylee Hatley | West Plains | 19.28.8 | Parkway West | 34pts |
| 2016 | Boys Barker | Ryan Parson | Farmington | 16:36.6 | Festus | 59pts |
| Boys Hartmann | Schuyler Ogden | Ste. Genevieve | 16:44.7 | Ste. Genevieve | 37pts | |
| Boys Borsa | Simon Gelber | Whitfield | 17:27.4 | Russellville | 83pts | |
| Girls Barker | Gemma Saaathoff | Hickman | 19:56.0 | Parkway West | 36pts | |
| Girls Hartmann | Samantha Kang | St. Francis Borgia | 20:15.3 | Helias Catholic | 53pts | |
| Girls Borsa | Julia McIntyre | New Haven | 20:28.8 | Father Tolton | 50pts |
| 2015 | Boys Barker | Simon Gelber | Whitfield | 17:00.70 | Fatima | 44pts |
| Boys Hartmann | Ben Naeger | Ste. Genevieve | 15:32.33 | Ste. Genevieve | 42pts | |
| Boys Borsa | Alec Haines | Lafayette | 15:53.19 | Festus | 54pts | |
| Girls Barker | Anna Massman | Fatima | 19:17.45 | Fatima | 22pts | |
| Girls Hartmann | Geneva Lee | M.I.C.D.S. | 19:44.46 | M.I.C.D.S. | 54pts | |
| Girls Borsa | Taylor Werner | Ste. Genevieve | 17:42.70 | Lafayette | 26pts |
| 2014 | Boys Barker | Nate Gelber | Whitfield | 16.38.14 | Fatima | 69pts |
| Boys Hartmann | Ben Naeger | Ste. Genevieve | 16:19.69 | Cape Notre Dame | 72pts | |
| Boys Borsa | Camden Barrett | West Plains | 15:55.92 | Festus | 36pts | |
| Girls Barker | Keri Burmester | Red Bud (IL) | 19:38.63 | Fatima | 52pts | |
| Girls Hartmann | Carolyn White | Festus | 19:33.86 | Festus | 63pts | |
| Girls Borsa | Maddie Leigh | Francis Howell | 19:12.00 | West Plains | 68pts |
| 2013 | Boys Barker | Tom Zeilman | Fatima | 17:32.73 | Fatima | 34pts |
| Boys Hartmann | Austin King | Potosi | 16:41.31 | Cape Notre Dame | 58pts | |
| Boys Borsa | Dylan Quisenberry | Lafayette | 16:06.62 | West Plains | 28pts | |
| Girls Barker | Deanna Deterding | Red Bud (IL) | 19:50.82 | Fatima | 36pts | |
| Girls Hartmann | Geneva Lee | M.I.C.D.S. | 20:52.87 | M.I.C.D.S. | 48pts | |
| Girls Borsa | Taylor Werner | Ste. Genevieve | 17:43.19 | Ste. Genevieve | 63pts |
| 2012 | Boys Barker | Drake Smelser | Herculaneum | 17:14.92 | Herculaneum | 48pts |
| Boys Hartmann | Kirk Smith | John Burroughs | 16:26.58 | Festus | 46pts | |
| Boys Borsa | Nathan Keown | Rock Bridge | 16:11.11 | West Plains | 65pts | |
| Girls Barker | Kaitlyn Fisher | Herculaneum | 18:27.63 | Herculaneum | 50pts | |
| Girls Hartmann | Taylor Werner | Ste. Genevieve | 18:00.20 | Ste. Genevieve | 25pts | |
| Girls Borsa | Maddy Brown | Parkway West | 19:05.68 | Francis Howell | 78pts |
| 2011 | Boys Barker | Brandon Shemonia | Scott City | 16:44.39 | Herculaneum | 65pts |
| Boys Hartmann | Sheldon Keence | St. Charles West | 17:04.86 | Cape N.D./Desoto | 118pts | |
| Boys Borsa | Drew Cargill | West Plains | 16:27.93 | West Plains | 40pts | |
| Girls Hartmann | Shelby Werner | Ste. Genevieve | 20:28.98 | Cape Notre Dame | 95pts | |
| Girls Borsa | Melissa Brown | Oakville | 19:28.75 | Lafayette | 47pts |
| 2010 | Boys Barker | Brandon Shemonia | Scott City | 16:47.60 | Herculaneum | 29pts |
| Boys Hartmann | Drew White | Festus | 16:44.27 | Festus | 64pts | |
| Boys Borsa | Drew Cargill | West Plains | 16:35.10 | West Plains | 74pts | |
| Girls Barker | Mary Moloney | Herculaneum | 21:30.80 | Herculaneum | 15pts | |
| Girls Hartmann | Emma Burditt | Hannibal | 20:06.15 | M.I.C.D.S | 99pts | |
| Girls Borsa | Jenny Govero | Rockwood Summit | 19:28.44 | Rockwood Summit | 78pts |
| 2009 | Boys Barker | Alex Mason | Herculaneum | 17:04.44 | Herculaneum | 36pts |
| Boys Hartmann | David Lambus | University City | 16:51.30 | Festus | 36pts | |
| Boys Borsa | Jake Lamke | Parkway West | 16:59.64 | Parkway West | 32pts | |
| Girls Barker | Saga Barzowski | Arcadia Valley | 19:48.71 | Herculaneum | 21pts | |
| Girls Hartmann | Sarah Jacobsen | Potosi | 19:30.31 | Festus | 94pts | |
| Girls Borsa | Colleen Quigley | Nerinx Hall | 19:17.21 | Rockwood Summit | 78pts |
| 2008 | Boys Barker | Alex Mason | Herculaneum | 17:13.51 | Herculaneum | 25pts |
| Boys Hartmann | Jacob Swearington | Potosi | 16:21.29 | Potosi | 52pts | |
| Boys Borsa | Nick Happe | Francis Howell North | 16:10.27 | Rogers (AR) | 52pts | |
| Girls Barker | Kelsie Hutsell | Willow Springs | 20:10.27 | Herculaneum | 52pts | |
| Girls Hartmann | Sarah White | Potosi | 19:43.46 | Ste. Genevive | 46pts | |
| Girls Borsa | Veronica Schabbing | Cape Central | 19:24.36 | Eureka | 63pts |
| 2007 | Boys Barker | Adam Prahlow | Lutheran North | 17:11.79 | Herculaneum | 30pts |
| Boys Hartmann | Adam Behnke | Lutheran South | 16:07.84 | Potosi | 52pts | |
| Boys Borsa | Eric Fernandez | Parkway West | 15:47.11 | Parkway West | 54pts | |
| Girls Barker | Kelsie Hutsell | Willow Springs | 20:52.04 | Liberty Benton | 40pts | |
| Girls Hartmann | Natalie Todd | Ladue | 18:59.09 | Ste. Genevive | 54pts | |
| Girls Borsa | Aimee Bonte | Rockwood Summit | 19:33.91 | Cape Central | 43pts |
| Year | Division | Runner | School | Winning Time | Team Winner | Team Points |
| 2006** | Boys 1-2A | Kyle Hendrix | Herculaneum | 17:54 | Herculaneum | 22pts |
| Boys 3A | Adam Behnke | Lutheran South | 16:21 | Ste. Genevieve | 49pts | |
| Boys 4A | Josh Thebeau | Potosi | 15:45 | Potosi | 15pts | |
| Girls 1-2A | Megan Arnold | Herculaneum | 20:49 | Herculaneum | 15pts | |
| Girls 3A | Alyssa Allison | Festus | 20:52 | Ste. Genevieve | 33pts | |
| Girls 4A | Amy Bonte | Rockwood Summit | 20:08 | Rockwood Summit | 27pts |
** In 2006, heavy storms caused the race to be cancelled on Saturday and held on an alternate date, resulting in many teams not being in attendance.
| 2005 | Boys 1-2A | Larry Paul | Wright City | 16:46 | Ste. Genevieve | 67pts |
| Boys 3A | Josh Mathis | Potosi | 16:21 | Potosi | 34pts | |
| Boys 4A | Ben Murphy-Baum | SLUH | 16:27 | Ft. Zumwalt South | 60pts | |
| Girls 1-2A | Meagan Hudson | Crystal City | 20:02 | Herculaneum | 31pts | |
| Girls 3A | Jessica Bollinger | Ste. Genevieve | 19:53 | Ste. Genevieve | 29pts | |
| Girls 4A | Katelyn Bastert | Carthage | 19:13 | Jefferson City | 63pts |
| 2004 | Boys 1-2A | Sean Swapp | Herculaneum | 17:27 | Herculaneum | 39pts |
| Boys 3A | Dustin Dixon | St. Clair | 16:22 | Potosi | 32pts | |
| Boys 4A | Tim Cornell | Columbia Hickman | 16:03 | West Plains | 45pts | |
| Girls 1-2A | Hillary Forman | Pembroke Hills | 20:38 | Herculaneum | 43pts | |
| Girls 4A | Merideth Snow | Eureka | 18:44 | West Plains | 45pts |
| 2003 | Boys 1-2A | Preston Lingo | Herculaneum | 17:27 | Herculaneum | 37pts |
| Boys 3A | Kyle Davis | Potosi | 16:31 | Potosi | 43pts | |
| Boys 4A | Ian McFarland | West Plains | 16:04 | West Plains | 54pts | |
| Girls 1-2A | Amber Warren | Lutheran High | 19:27 | Herculaneum | 60pts | |
| Girls 3A | Jennifer Woods | Warrensburg | 20:05 | Warrensburg | 32pts | |
| Girls 4A | Jennifer Harper | West Plains | 18:59 | West Plains | 33pts |
| 2002 | Boys 1-2A | Andrew Almany | Licking | 17:03 | Herculaneum | 35pts |
| Boys 3A | Kyle Davis | Potosi | 16:32 | Potosi | 53pts | |
| Boys 4A | Adam Perkins | Liberty | 15:41 | Liberty | 28pts | |
| Girls 1-2A | Amber Warren | Lutheran High | 20:44 | Herculaneum | 50pts | |
| Girls 3A | Krista Merrill | Potosi | 19:37 | Warrensburg | 30pts | |
| Girls 4A | Katy Bundy | Marquette | 19:21 | Liberty | 75pts |
| 2001 | Boys 1-2A | Edie Higgins | Pembroke Hills | 17:19 | Priory | 60pts |
| Boys 3A | Daniel Strackeljahn | Highland | 16:25 | Chaminade | 65pts | |
| Boys 4A | Stephen Pifer | Edwardsville | 15:57 | West Plains | 48pts | |
| Girls 1-2A | Amber Warren | Lutheran High | 20:07 | Herculaneum | 68pts | |
| Girls 3A | Shannon Leinert | Eureka | 20:07 | St. Charles West | 82pts | |
| Girls 4A | Trista McKee | West Plains | 19:49 | West Plains | 48pts |
| Year | Division | Runner | School | Winning Time | Team Winner | Team Points |
| 2000 | Blue | Aaron Grimes | Farmington | 16:44.3 | Ladue | 138pts |
| Gold | Miles Brown | Glendale | 15:58.4 | DeSmet | 95pts | |
| Girls Blue | Allison Smith | Pembroke Hills | 19:48.2 | Liberty Benton | 79pts | |
| Girls Gold | Laura Kennedy | Lafayette | 19:35.1 | Kirkwood | 39pts |
| 1999 | Blue | Walker Eye | Potosi | 16:26.5 | Eureka | 131pts |
| Gold | Jason Sandfort | West Plains | 16:24.8 | Jefferson City | 110pts | |
| Girls Blue | Jenny Burke | St. Dominic | 19:54.0 | St. Charles West | 145pts | |
| Girls Gold | Amanda Murcak | West Plains | 19:39.4 | West Plains | 57pts |
| 1998 | Blue | Scott Smith | Willow Springs | 16:44.1 | Lutheran South | 120pts |
| Gold | Jason Sandfort | West Plains | 16:46.9 | West Plains | 90pts | |
| Girls Blue | Katie Hoffman | N.D. DeSion | 19:35.6 | N.D. DeSion | 69pts | |
| Girls Gold | Karen Rogers | Kirkwood | 19:47.1 | West Plains | 36pts |
| 1997 | Blue | Cabb Geinter | Highland | 16:35.6 | Willow Springs | 84pts |
| Gold | Billy Hibdon | Jefferson City | 16:28.6 | Jefferson City | 33pts | |
| Girls Blue | Jenny Noelken | Duchesne | 20:32.7 | Duchese | 68pts | |
| Girls Gold | Kristen McFerran | St. Charles West | 19:06.2 | West Plains | 66pts |
| 1996 | Blue | Scott Smith | Willow Springs | 17:08 | Willow Springs | 97pts |
| Gold | Steve Williamson | Kirkwood | 16:26 | Jefferson City | 35pts | |
| Girls Blue | Kristen Bruening | Duchesne | 20:11 | Visitation | 72pts | |
| Girls Gold | Melissa Sappa | Oakville | 19:09 | West Plains | 87pts |
| Year | Division | Runner | School | Winning Time | Team Winner | Team Points |
| 1995 | Blue | Mike Perez | Herculaneum | 16:39 | St. Dominic | 186pts |
| Gold | Tom Breckinridge | St. Charles | 16:07 | Francis Howell | 103pts | |
| Girls | Catherine Wright | Oakville | 18:49 | West Plains | 69pts |
| 1994 | Blue | Jack Preus | Lutheran South | 15:58 | North County | 97pts |
| Gold | Sean Carlson | West Plains | 16:20 | West Plains | 37pts | |
| Girls | Catherine Wright | Oakville | 19:06 | West Plains | 42pts |
| 1993 | Blue | Ryan Pirtle | North County | 17:30 | North County | 63pts |
| Gold | Sean Carlson | West Plains | 17:35 | West Plains | 36pts | |
| Girls | Sherry Lange | West Plains | 20:37 | West Plains | 56pts |
| 1992 | Blue | Jeremy Struttman | St. Pius X | 16:20 | North County | 135pts |
| Gold | Chad Williamson | West Plains | 16:17 | West Plains | 47pts | |
| Girls | Misty McGhee | West Plains | 19:29 | West Plains | 65pts |
| 1991 | Blue | Mike Moisio | Country Day | 17:00 | St. Charles | 116pts |
| Gold | Chad Williamson | West Plains | 16:29 | West Plains | 37pts | |
| Girls | Lisa Brown | West Plains | 19:13 | West Plains | 61pts |
| 1990 | Blue | James Hunn | St. Dominic | 17:07 | Valley Park | 133pts |
| Gold | Chad Williamson | West Plains | 16:15 | Parkway West | 52pts | |
| Girls | Lisa Brown | West Plains | 19:38 | West Plains | 77pts |
| 1989 | Blue | Skeeter Rankins | Herculaneum | 16:07.4 | St. Dominic | 72pts |
| Gold | Terry Ryan | DeSmet | 16:12.1 | West Plains | 49pts | |
| Girls | Kally Fischer | Oakville | 19:18.4 | West Plains | 46pts |
| 1988 | Blue | Skeeter Rankins | Herculaneum | 16:26 | Herculaneum | 114pts |
| Gold | Danny Tuttle | West Plains | 16:26 | West Plains | 44pts | |
| Girls | Melissa Rice | Lafayette | 18:56 | West Plains | 46pts |
| 1987 | Blue | Rob Pind | Herculaneum | 16:26 | St. Clair | 40pts |
| Gold | Mike Donahue | West Plains | 16:18 | West Plains | 19pts | |
| Girls | Melissa Rice | Lafayette | 18:57 | West Plains | 28pts |
| 1986 | Blue | Bryant Wright | Festus | 17:02 | Festus | 68pts |
| Gold | Chris Woodard | SLUH | 16:41 | Hazelwood West | 69pts | |
| Girls | Dana McReynolds | Hazlewood | 20:42 | West Plains | 53pts |
| 1985 | Blue | Tim Keller | Crystal City | 16:10.5 | St. Charles West | 111pts |
| Gold | Mark Stasney | West Plains | 16:02 | West Plains | 29pts | |
| Girls | Val Sauer | Rolla | 19:43 | West Plains | 59pts |
| 1984 | Blue | Eric Van Matre | Rolla | 16:26 | Rolla | 85pts |
| Gold | Chris Borsa | CBC | 15:58 | West Plains | 61pts | |
| Girls | Mary Lee Bankhead | Lindbergh | 20:06 | Lindbergh | 64pts |
| 1983 | Blue | Andy Prater | Sullivan | 16:39 | Lutheran South | 83pts |
| Gold | Brian Radle | Fox | 15:16 | Desmet | 58pts | |
| Girls | Val Sauer | Rolla | 19:37 | Herculaneum | 92pts |
| 1982 | Blue | Greg Reecht | Crystal City | 17:00 | Crystal City | 44pts |
| Gold | Chris Zinn | West Plains | 15:44 | West Plains | 133pts | |
| Girls | Jill Kingsbury | Washington | 19:00 | Eureka | 86pts |
| 1981 | Blue | Jim Jennings | Crystal City | 16:31.0 | Crystal City | 40pts |
| Gold | Chris Zinn | West Plains | 16:12.0 | West Plains | 120pts | |
| Girls | Jill Kingsbury | Washington | 19:29.7 | Hazelwood Central | 181pts |
| 1980 | Blue | Mike Graff | Sullivan | 16:24.8 | Herculaneum | 32pts |
| Gold | Dan Graf | DeSmet | 16:05.1 | Lindbergh | 103pts | |
| Girls | Jill Kingsbury | Washington | 18:37 | Kirkwood | 81pts |
| Year | Division | Runner | School | Winning Time | Team Winner | Team Points |
| 1979 | Blue | Jeff Elder | Herculaneum | 13:04 | Prep North | 65pts |
| Gold | Tom Becker | Ritenour | 12:45.1 | Lindbergh | 72pts | |
| 1978 | Blue | Ed Neff | Hancock | 13:15 | Prep North | 75pts |
| Gold | Don Bene | Hazelwood Central | 12:35 | McCluer North | 111pts | |
| 1977 | Blue | Mark Whalley | Principia | 12:50 | Lutheran South | 47pts |
| Gold | Roger Doherty | Ritenour | 12:42.7 | McCluer North | 63pts | |
| 1976 | Blue | Dave Smith | Hancock | 12:42.8 | Herculaneum | 53pts |
| Gold | Steve Beasley | Pattonville | 12:42.7 | Pattonville | 69pts | |
| 1975 | Blue | Tom Stutz | Prep North | 13:13 | Prep North | 54pts |
| Gold | Don Shell | Northwest | 12:45 | Northwest | 71pts |
| Year | Division | Runner | School | Winning Time | Team Winner | Team Points |
| 1974 | Blue | Jim Minor | Prep North | 10:06.7 | Prep North | 66pts |
| Gold | Bill Lowry | Parkway North | 9:56.8 | Parkway North | 44pts | |
| 1973 | Blue | Mark Randolph | Hancock | 10:13 | Herculaneum | 60pts |
| Gold | Rick Fitzpatrich | SLUH | 10:01 | Northwest | 68pts | |
| 1972 | Blue | Paul Lammert | Hillsboro | 10:27 | Maplewood | 113pts |
| Gold | Alton Davis | Hazelwood | 9:56 | Lindbergh | 71pts | |
| 1971 | Blue | Ron Harmon | Berkeley | 10:15 | Lutheran South | 72pts |
| Gold | Wolfgang Kashner | Kirkwood | 9:52 | Northwest | 61pts |
| Year | Runner | School | Winning Time | Team Winner | Team Points |
| 1970 | Bill Parmelee | Parkway Central | 10:02.0 | Parkway Central | 39pts |
| 1969 | Bob Peilikan | Bishop DuBourg | 9:59.4 | Kirkwood | 30pts |
| 1968 | Bob Peilikan | Bishop DuBourg | 10:24.8 | Lindbergh | 87pts |
| 1967 | Russ Keucker | Lutheran South | 10:00.7 | Lindbergh | 93pts |
| 1966 | Tom Westbrook | Ritenour | 10:39.6 | Lindbergh | 69pts |
| 1965 | Mel Cotton | Lutheran South | 10:38.3 | Lutheran South | 72pts |
| 1964 | Mel Cotton | Lutheran South | 10:35.1 | Clayton | 62pts |
| 1963 | Len Corso | Mercy | 10:45.7 | Mercy | 47pts |
