| Year | Class | Student | School | Score |
| 2023 | 1 | Riley Blay | West Nodaway | 15:48.20 |
| 2023 | 2 | Reed Layton | Woodland | 16:25.20 |
| 2023 | 3 | Ben Chance | Bowling Green | 15:25.20 |
| 2023 | 4 | Isaac Rivera | Lincoln College Prep | 14:54.60 |
| 2023 | 5 | Luke Sievers | Rock Bridge | 14:51.90 |
| 2022 | 1 | Riley Blay | West Nodaway | 16:28.20 |
| 2022 | 2 | Conner Diaz | Steelville | 16:15.00 |
| 2022 | 3 | Connor Burns | Southern Boone | 15:01.20 |
| 2022 | 4 | Josh Allison | Hillsboro | 15:38.90 |
| 2022 | 5 | Sage Wilde | Liberty North | 15:05.90 |
| 2021 | 1 | Riley Blay | West Nodaway | 16:05.90 |
| 2021 | 2 | Tanner Talley | New Covenant Academy | 15:32.50 |
| 2021 | 3 | Connor Burns | Southern Boone | 15:13.50 |
| 2021 | 4 | Caleb Lind | Lutheran St. Charles | 15:15.20 |
| 2021 | 5 | Andrew Hauser | Rock Bridge | 14:52.70 |
| 2020 | 1 | Tyler Blay | West Nodaway | 16:30.30 |
| 2020 | 2 | Sam Shuman | Spokane | 16:03.60 |
| 2020 | 3 | Daelan Ackley | El Dorado Springs | 15:41.10 |
| 2020 | 4 | Riley Simpson | West Plains | 15:39.50 |
| 2020 | 5 | Matthew Hauser | Rock Bridge | 15:34.50 |
| 2019 | 1 | Jace Cavness | The Fulton School at St. Albans | 16:39.70 |
| 2019 | 2 | Daelen Ackley | El Dorado Springs | 15:39.00 |
| 2019 | 3 | Michael Rebello | Excelsior Springs | 15:29.40 |
| 2019 | 4 | Wesley Porter | Rockhurst | 15:07.40 |
| 2018 | 1 | Chase Ratliff | Weaubleau | 17:10.73 |
| 2018 | 2 | Kolin Overstreet | Lamar | 16:34.70 |
| 2018 | 3 | Maxwell McDaniel | Festus | 16:12.10 |
| 2018 | 4 | Christian Baker | Kirkwood | 15:42.03 |
| 2017 | 1 | Easton Sabala | Hermitage | 16:43.33 |
| 2017 | 2 | Cornelius Caleb | Saxony Lutheran | 16:22.55 |
| 2017 | 3 | Edward Wilhite | Warrensburg | 15:42.27 |
| 2017 | 4 | Victor Mugeche | Blue Springs | 15:29.13 |
| 2016 | 1 | Riley Gorham | Hardin-Central | 16:43.28 |
| 2016 | 2 | Simon Gelber | Whitfield | 16:24.62 |
| 2016 | 3 | Stephen Kielhofner | Springfield Catholic | 15:36.61 |
| 2016 | 4 | Austin Hindman | Lafayette (St. Joseph) | 15:22.30 |
| 2015 | 1 | Riley Gorham | Hardin-Central | 16:43.37 |
| 2015 | 2 | Stephen Kielhofner | Springfield Catholic | 16:13.52 |
| 2015 | 3 | Ben Naeger | Ste. Genevieve | 15:34.56 |
| 2015 | 4 | Devin Meyrer | Lafayette (St. Joseph) | 15:25.42 |
| 2014 | 1 | Seth Brown | La Plata | 16:41.60 |
| 2014 | 2 | Nate Gelber | Whitfield | 16:04.62 |
| 2014 | 3 | Michael Karls | Festus | 15:23.80 |
| 2014 | 4 | Stephen Mugeche | Blue Springs | 15:32.23 |
| 2013 | 1 | Seth Brown | La Plata | 16:51.09 |
| 2013 | 2 | Kaden Overstreet | Lamar | 16:35.22 |
| 2013 | 3 | Tyler Gillam | Festus | 16:24.98 |
| 2013 | 4 | Noah Kauppila | Marquette | 15:22.34 |
| 2012 | 1 | Tyler Rush | Linn | 16:33.99 |
| 2012 | 2 | Deko Ricketts | Barstow | 17:02.45 |
| 2012 | 3 | Amos Bartelsmeyer | MICDS | 16:24.98 |
| 2012 | 4 | Simon Belete | Blue Springs | 15:48.16 |
| 2011 | 1 | Kaleb Wilson | Linn | 17:01.32 |
| 2011 | 2 | Brandon Shemonia | Scott City | 16:20.34 |
| 2011 | 3 | Drew White | Festus | 16:05.71 |
| 2011 | 4 | Caleb Wilfong | Rock Bridge | 15:54.13 |
| 2010 | 1 | Caleb Hoover | College Heights Christian | 16:11.11 |
| 2010 | 2 | Drew Keefer | St. Pius X (Kansas City) | 16:07.01 |
| 2010 | 3 | Daniel Everett | Westminster Christian Academy | 15:52.13 |
| 2010 | 4 | Zach Herriott | Rockhurst | 15:30.55 |
| 2009 | 1 | Caleb Hoover | College Heights Christian | 16:22.00 |
| 2009 | 2 | Caleb Sutton | Arcadia Valley | 17:15.00 |
| 2009 | 3 | Maksim Korolev | Harrisonville | 15:48.00 |
| 2009 | 4 | Danny Thater | Kickapoo | 16:12.00 |
| 2008 | 1 | Trenton Morris | College Heights Christian | 16:39.00 |
| 2008 | 2 | Tyler Compton | Buffalo | 16:44.00 |
| 2008 | 3 | Jacob Swearingen | Potosi | 15:38.00 |
| 2008 | 4 | Kevin Colon | Lee's Summit West | 15:51.00 |
| 2007 | 1 | Ethan Beaver | College Heights Christian | 16:51.00 |
| 2007 | 2 | Max Storms | O'Hara | 16:39.00 |
| 2007 | 3 | Jacob Swearingen | Potosi | 16:00.00 |
| 2007 | 4 | Eric Fernandez | Parkway South | 15:50.00 |
| 2006 | 1 | Grant Brown | Lone Jack | 16:54.10 |
| 2006 | 2 | Justin Brown | Mountain Grove | 16:54.50 |
| 2006 | 3 | Josh Thebeau | Potosi | 15:37.90 |
| 2006 | 4 | Kyle Rood | Ft. Zumwalt South | 15:38.10 |
| 2005 | 1 | David Goeglein | Lutheran (Kansas City) | 16:52.10 |
| 2005 | 2 | Sean Swapp | Herculaneum | 17:00.10 |
| 2005 | 3 | Josh Mathis | Potosi | 15:41.60 |
| 2005 | 4 | Ben Brammeier | Parkway South | 15:59.50 |
| 2004 | 1 | David Goeglein | Lutheran (Kansas City) | 17:41.10 |
| 2004 | 2 | Larry Paul | Wright City | 16:51.50 |
| 2004 | 3 | Dustin Dixon | St. Clair | 16:28.30 |
| 2004 | 4 | Tim Cornell | Hickman | 16:21.20 |
| 2003 | 1 | Daniel Moore | West Platte | 17:13.30 |
| 2003 | 2 | Dusty Kime | Monett | 16:45.30 |
| 2003 | 3 | Kyle Davis | Potosi | 16:25.60 |
| 2003 | 4 | Tim Cornell | Hickman | 16:01.30 |
| 2002 | 1 | Colten Green | Macks Creek | 16:47.10 |
| 2002 | 2 | Dusty Kime | Monett | 16:57.80 |
| 2002 | 3 | Kenneth Bowling | Republic | 16:26.40 |
| 2002 | 4 | Adam Perkins | Liberty | 16:09.80 |
| 2001 | 1A | Colten Green | Macks Creek | 16:38.20 |
| 2001 | 2A | Nathan Poindexter | Bolivar | 16:29.30 |
| 2001 | 3A | Charlie Bromley | Carl Junction | 16:22.10 |
| 2001 | 4A | Adam Perkins | Liberty | 15:59.80 |
| 2000 | 1A | Tommy Neal | Leeton | 16:33.90 |
| 2000 | 2A | Ben Glass | Principia | 16:58.10 |
| 2000 | 3A | Aaron Grimes | Farmington | 16:18.50 |
| 2000 | 4A | Jason Sandfort | West Plains | 15:43.20 |
| 1999 | 1A | Tommy Neal | Leeton | 17:11.70 |
| 1999 | 2A | Jordan Millam | Clinton | 16:17.90 |
| 1999 | 3A | Walker Eye | Potosi | 16:06.80 |
| 1999 | 4A | Matt Tegenkamp | Lee's Summit | 15:26.70 |
| 1998 | 1A | Richie Kientzy | Valley Park | 16:37.30 |
| 1998 | 2A | Scott Smith | Willow Springs | 16:12.00 |
| 1998 | 3A | Stewart Kimball | Eureka | 16:21.50 |
| 1998 | 4A | Mike Krull | Christian Brothers College | 16:08.00 |
| 1997 | 1A-2A | Scott Smith | Willow Springs | 16:42.20 |
| 1997 | 3A | Jason Edwards | Logan-Rogersville | 16:21.70 |
| 1997 | 4A | Steve Wade | Truman | 16:08.10 |
| 1996 | 1A-2A | Bryan Fugate | St. Mary's (Independence) | 17:01.40 |
| 1996 | 3A | Mike Pitts | Central (Springfield) | 16:09.20 |
| 1996 | 4A | Adam MacDowell | Parkway South | 16:14.70 |
| 1995 | 1A-2A | Bryan Fugate | St. Mary's (Independence) | 17:08.10 |
| 1995 | 3A | Mike Perez | Herculaneum | 16:31.90 |
| 1995 | 4A | Tom Breckenridge | St. Charles West | 15:55.00 |
| 1994 | 1A-2A | Chris Fugate | St. Mary's (Independence) | 17:55.90 |
| 1994 | 3A | Jack Preus | Lutheran South | 16:37.10 |
| 1994 | 4A | Sean Carlson | West Plains | 16:31.00 |
| 1993 | 1A-2A | Michael Rymer | Pembroke Hill | 17:36.80 |
| 1993 | 3A | Don Conrad | MICDS | 16:35.50 |
| 1993 | 4A | Sean Carlson | West Plains | 16:21.50 |
| 1992 | 1A-2A | Ray Hughes | Cuba | 17:13.30 |
| 1992 | 3A | Craig Maxwell | St. Charles | 16:44.10 |
| 1992 | 4A | Randon Richards | Blue Springs | 16:02.80 |
| 1991 | 1A-2A | Brent Burroughs | Pembroke Hill | 17:22.60 |
| 1991 | 3A | John Roberts | Southwest Math and Science | 16:45.80 |
| 1991 | 4A | Randon Richards | Blue Springs | 16:53.20 |
| 1990 | 1A-2A | David Shanholtzer | Springfield Catholic | 17:15.50 |
| 1990 | 3A | Brennan Graves | Center | 16:49.40 |
| 1990 | 4A | Jason Gauert | Lee's Summit | 16:03.20 |
| 1989 | 1A-2A | Jim Hendrix | Valley Park | 17:34.00 |
| 1989 | 3A | DeWayne Miner | Bolivar | 16:22.30 |
| 1989 | 4A | Jason Gauert | Lee's Summit | 16:13.90 |
| 1988 | 1A-2A | Brent Ward | Russellville | 17:39.20 |
| 1988 | 3A | DeWayne Miner | Bolivar | 16:31.40 |
| 1988 | 4A | Michael Cox | Hannibal | 16:12.40 |
| 1987 | 1A-2A | Matt Bowen | Viburnum | 17:29.90 |
| 1987 | 3A | Robbie Pind | Herculaneum | 16:49.50 |
| 1987 | 4A | Bill Sitton | Ruskin | 16:14.40 |
| 1986 | 1A-2A | Greg Starr | Russellville | 17:31.40 |
| 1986 | 3A | Phil Bryne | O'Hara | 16:44.10 |
| 1986 | 4A | John Meyers | Poplar Bluff | 16:34.20 |
| 1985 | 1A-2A | Tim Keller | Crystal City | 16:30.80 |
| 1985 | 3A | Rob McCarter | Warrensburg | 16:57.60 |
| 1985 | 4A | Jon Hatley | West Plains | 15:58.70 |
| 1984 | 1A-2A | Tim Keller | Crystal City | 16:55.00 |
| 1984 | 3A | Phil Bryne | O'Hara | 16:46.70 |
| 1984 | 4A | Chris Borsa | Christian Brothers College | 15:41.70 |
| 1983 | 1A-3A | Joe Falcon | Belton | 15:57.50 |
| 1983 | 4A | Chris Zinn | West Plains | 15:46.70 |
| 1982 | 1A-3A | Don Sawyer | Herculaneum | 16:25.50 |
| 1982 | 4A | Chris Zinn | West Plains | 15:55.30 |
| 1981 | 1A-3A | Jeff Pigg | Logan-Rogersville | 16:15.50 |
| 1981 | 4A | Chris Zinn | West Plains | 16:19.10 |
| 1980 | 1A-3A | Jeff Pigg | Logan-Rogersville | 16:35.70 |
| 1980 | 4A | Kirk Sloan | Rock Bridge | 16:11.00 |
| 1979 | 1A-3A | Jeff Elder | Herculaneum | 13:13.20 |
| 1979 | 4A | Reynold Middleton | Northeast (Kansas City) | 12:51.60 |
| 1978 | A | Brian Stotler | Herculaneum | 13:28.00 |
| 1978 | AA | Brian Blackford | Lindbergh | 13:09.40 |
| 1977 | A | Mark Whalley | Principia | 13:10.30 |
| 1977 | AA | Roger Doherty | Ritenour | 13:15.80 |
| 1976 | A | Mark Whalley | Principia | 12:24.50 |
| 1976 | AA | Bryce Allmon | Jefferson City | 12:13.60 |
| 1975 | A | David Smith | Hancock | 13:07.30 |
| 1975 | AA | Don Shell | Northwest (Cedar Hill) | 12:38.00 |
| 1974 | | David Cooper | Jefferson City | 9:44.00 |
| 1973 | | Brad Hawthorne | Lee's Summit | 9:46.70 |
| 1972 | | John Prasuhn | Northwest (Cedar Hill) | 9:48.00 |
| 1971 | | Mark Kimball | Riverview Gardens | 9:57.20 |
| 1970 | | Don Overton | Parkway West | 9:45.00 |
| 1969 | | Bob Pelikan | Bishop DuBourg | 10:10.00 |
| 1968 | | Steve Wilson | Southwest (Livingston County) | 9:58.50 |
| 1967 | | Kerry Hogan | Kirkwood | 9:49.90 |
| 1966 | | John Baldwin | Assumption | 9:50.50 |
| 1965 | | John Baldwin | O'Fallon Technical High School | 9:50.50 |
| 1964 | | Bill Young | Riverview Gardens | 10:08.60 |
| 1963 | | Jim Olson | Kirkwood | 9:39.90 |
| 1962 | | Dennis Hudson | Sumner | 10:03.30 |
| 1961 | | Mike Hensgen | Kirkwood | 10:22.70 |
| 1960 | | Jerry Dienberger | St. Louis University | 9:50.10 |
| 1959 | | Louis Virdure | Vashon | 9:51.50 |
| 1958 | | Louis Virdure | Vashon | 9:54.60 |
| 1957 | | Jim Harmon | Beaumont | 10:02.40 |
| 1956 | | Ron Schoen | Beaumont | 10:32.10 |
| 1955 | | Ronald Gregory | Sumner | 9:50.40 |
| 1954 | | Ronald Gregory | Sumner | 10:35.50 |
| 1953 | | Jim Shepard | Pacific | 9:11.40 |
| 1952 | | Joe Underwood | Central (Springfield) | 9:27.50 |
| 1951 | | Keith Bacon | Central (Springfield) | 9:35.70 |
| 1950 | | Richard Gregory | Sumner | 9:48.60 |
| 1949 | | Bob Lindquist | Cleveland NJROTC | 9:43.30 |