| Rank | Time | Student | Grade | School | Year | |
| 1 | 4:03.54 | Jason Pyrah | | Willard | 1987 | Class 3A |
| 2 | 4:05.03 | Jason Pyrah | | Willard | 1986 | Class 3A |
| 3 | 4:08.03 | Joe Falcon | | Belton | 1984 | Class 3A |
| 4 | 4:08.14 | Adam Perkins | | Liberty | 2002 | |
| 5 | 4:08.31 | Brian Radle | | Fox | 1984 | Class 4A |
| 6 | 4:09.41 | Spencer Bryan Haik | | Glendale | 2014 | Class 4 |
| 7 | 4:09.69 | Austin Patrick Hindman | | Lafayette (Wildwood) | 2017 | Class 5 |
| 8 | 4:10.97 | Dustan Alexander Davidson | | St. Louis University | 2016 | Class 5 |
| 9 | 4:11.58 | Alec Christian Haines | | Lafayette (Wildwood) | 2015 | Class 5 |
| 10 | 4:15.07 | Caleb Hoover | | College Heights Christian | 2009 | Class 2 |
| 11 | 4:15.41 | Danny Bryant | | Russellville | 1980 | Class 2 |
| 12 | 4:15.94 | Jim Jennings | | Crystal City | 1982 | Class 2 |
| 13 | 4:21.88 | Riley P Gorham | | Hardin-Central | 2016 | Class 1 |
| 14 | 4:22.40 | Riley P Gorham | | Hardin-Central | 2017 | Class 1 |
| 15 | 4:22.94 | Seth Summerside | | College Heights Christian | 2001 | Class 1 |