| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 18 | 12 | Dalton Gleeson | 16:14.4PR | MO | Hermann | Nov 5
| MSHSAA Class 3 State XC Championships |
| 2. | 17 | 12 | Dominick Beine | 16:52.3PR | MO | Union | Nov 6
| MSHSAA Class 4 State XC Championships |
| 3. | | 11 | Case Busse | 17:38.0 | MO | St. Clair | Sep 24
| Belle Invitational |
| 4. | | 11 | Gabriel Hoekel | 17:39.5 | MO | Union | Sep 19
| Festus Bowles Invitational |
| 5. | 18 | 12 | Austin Terry | 17:41.4PR | MO | Hermann | Oct 31
| MSHSAA Class 1, 2, 3 District 3 - Bowling Gre... |
| 6. | | 12 | Brayden Brown | 17:58.2 | MO | Hermann | Oct 31
| MSHSAA Class 1, 2, 3 District 3 - Bowling Gre... |
| 7. | | 10 | Aiden Kirk | 17:58.7PR | MO | Sullivan | Sep 17
| Steelville MS/HS Invitational |
| 8. | | 10 | Nicholas Hunkins | 18:09.0 | MO | Pacific | Oct 6
| Hermann Invitational |
| 9. | | 11 | Collin Haley | 18:12.7 | MO | Pacific | Sep 19
| Festus Bowles Invitational |
| 10. | | 10 | Aiden Kirk | 18:15.3 | MO | Sullivan | Sep 26
| Gans Creek Classic |
| 11. | 18 | 12 | Cameron O'Neal | 18:24.4 | MO | Owensville | Sep 19
| Bismarck Invitational |
| 12. | | 11 | Logan Williams | 18:27.7 | MO | New Haven | Nov 6
| MSHSAA Class 2 State XC Championships |
| 13. | | 11 | Tavis Harris | 18:29.1 | MO | Hermann | Oct 31
| MSHSAA Class 1, 2, 3 District 3 - Bowling Gre... |
| 14. | | 11 | Jacob Breedlove | 18:29.8 | MO | Owensville | Sep 19
| Bismarck Invitational |
| 15. | | 12 | Peter Giles | 18:31.3 | MO | Hermann | Nov 5
| MSHSAA Class 3 State XC Championships |
| 16. | 17 | 11 | Benjamin Brunjes | 18:31.4 | MO | Pacific | Sep 19
| Festus Bowles Invitational |
| 17. | | 11 | Joseph Burns | 18:34.3PR | MO | St. James | Sep 17
| Steelville MS/HS Invitational |
| 18. | | 9 | Jackson Poehlman | 18:40.1 | MO | Hermann | Oct 31
| MSHSAA Class 1, 2, 3 District 3 - Bowling Gre... |
| 19. | | 12 | Michael Giles | 18:42.8 | MO | Hermann | Nov 5
| MSHSAA Class 3 State XC Championships |
| 20. | | 12 | Hayden Monroe | 18:43.9 | MO | Union | Sep 19
| Festus Bowles Invitational |
| 21. | | 12 | Diego Orozco | 18:51.3PR | MO | Union | Sep 5
| New Haven High School CC Invitational |
| 22. | | 11 | Frederic Zheng | 18:57.2 | MO | Owensville | Sep 19
| Bismarck Invitational |
| 23. | 14 | 9 | Luke Shields | 19:00.2 | MO | St. James | Nov 5
| MSHSAA Class 3 State XC Championships |
| 24. | | 9 | Lucas Hoekel | 19:06.3 | MO | Union | Oct 6
| Hermann Invitational |
| 25. | | 11 | Hunter Tallent | 19:09.0 | MO | New Haven | Oct 13
| Owensville HS Invitational |
| 26. | | 10 | Andrew Rethemeyer | 19:12.5 | MO | New Haven | Sep 30
| St. James XC Invitational |
| 27. | | 10 | Joseph Gebel | 19:20.7 | MO | Pacific | Sep 19
| Festus Bowles Invitational |
| 28. | | 12 | Kaleb Means | 19:21.2 | MO | Hermann | Oct 6
| Hermann Invitational |
| 29. | | 11 | Harm Rademacher | 19:23.8 | MO | Owensville | Nov 5
| MSHSAA Class 3 State XC Championships |
| 30. | | 12 | Austin Tobben | 19:27.7PR | MO | St. Clair | Nov 6
| MSHSAA Class 4 State XC Championships |
| 31. | | 9 | Thomas Perkins | 19:36.8 | MO | St. Clair | Sep 24
| Belle Invitational |
| 32. | | 11 | Charlie Roth | 19:36.9 | MO | New Haven | Oct 31
| MSHSAA Class 2 District 4 - Linn |
| 33. | | 9 | Trigg Lindahl | 19:39.1 | MO | Hermann | Oct 6
| Hermann Invitational |
| 34. | | 9 | Nolan Gebel | 19:42.7 | MO | Pacific | Nov 6
| MSHSAA Class 4 State XC Championships |
| 35. | | 11 | Dylan Mooney | 19:43.3 | MO | Pacific | Sep 19
| Festus Bowles Invitational |
| 36. | | 11 | Cody Garver | 19:45.1PR | MO | St. James | Sep 17
| Steelville MS/HS Invitational |
| 37. | | 9 | Charles Schutt | 19:49.3PR | MO | Hermann | Sep 26
| Gans Creek Classic |
| 38. | | 10 | Jonathan Brewer | 19:58.4 | MO | St. Clair | Oct 24
| Fatima Blue and Gold |
| 39. | 15 | 10 | Trevor Shockley | 19:59.8 | MO | Owensville | Sep 19
| Bismarck Invitational |
| 40. | | 11 | Braedn Stone | 20:06.2 | MO | Owensville | Sep 24
| Belle Invitational |
| 41. | | 10 | Lucas Morgan | 20:10.3 | MO | Owensville | Sep 19
| Bismarck Invitational |
| 42. | | 12 | Woodrow Heldt | 20:13.1 | MO | Hermann | Oct 6
| Hermann Invitational |
| 43. | | 12 | Matthew Otten | 20:20.6 | MO | New Haven | Oct 31
| MSHSAA Class 2 District 4 - Linn |
| 44. | | 9 | Felix Guerrero | 20:21.1 | MO | Owensville | Oct 6
| Hermann Invitational |
| 45. | | 10 | Robert Morefield | 20:23.1PR | MO | Sullivan | Sep 17
| Steelville MS/HS Invitational |
| 46. | | 10 | Ayden Treece | 20:25.4PR | MO | Sullivan | Sep 17
| Steelville MS/HS Invitational |
| 47. | | 9 | Aiden Kern | 20:29.5 | MO | St. Clair | Oct 24
| Fatima Blue and Gold |
| 48. | | 10 | Noah Holtmeyer | 20:30.2 | MO | Owensville | Oct 6
| Hermann Invitational |
| 49. | | 11 | Ben Berkemeyer | 20:32.8 | MO | Hermann | Oct 6
| Hermann Invitational |
| 50. | | 9 | Tristan Davis | 20:34.1 | MO | Owensville | Oct 6
| Hermann Invitational |
| 51. | | 11 | Joe Burns | 20:36.6 | MO | St. James | Oct 31
| MSHSAA Class 3 District 4 - Linn |
| 52. | | 10 | Noah Carrico | 20:37.3 | MO | Pacific | Nov 6
| MSHSAA Class 4 State XC Championships |
| 53. | | 9 | Ethan Harris | 20:38.3 | MO | Owensville | Oct 6
| Hermann Invitational |
| 54. | | 9 | Luke Wade | 20:44.6PR | MO | Pacific | Nov 6
| MSHSAA Class 4 State XC Championships |
| 55. | | 12 | John Davenport cort... | 20:50.3 | MO | St. Clair | Sep 24
| Belle Invitational |
| 56. | | 10 | Aiden McCormack | 20:51.7 | MO | St. Clair | Oct 13
| Owensville HS Invitational |
| 57. | | 12 | Zachary Deardeuff | 20:52.9 | MO | St. James | Oct 31
| MSHSAA Class 3 District 4 - Linn |
| 58. | | 11 | Chase Walker | 20:57.8 | MO | Sullivan | Oct 31
| MSHSAA Class 4, 5 District 2 - Sullivan |
| 59. | | 9 | Ayden Elder | 20:59.8PR | MO | Hermann | Sep 24
| Belle Invitational |
| 60. | 14 | 9 | Quinn Shultz | 21:03.7PR | MO | St. James | Sep 17
| Steelville MS/HS Invitational |
| 61. | | 12 | Daniel Gerloff | 21:09.5 | MO | Hermann | Oct 6
| Hermann Invitational |
| 62. | | 10 | Jonathan Oloyed | 21:14.0PR | MO | St. Clair | Sep 24
| Belle Invitational |
| 63. | | 9 | Aiden Borgmann | 21:16.5 | MO | Union | Sep 12
| Forest Park XC Invitational |
| 64. | | 10 | Kainalu Souza | 21:28.5 | MO | St. Clair | Oct 24
| Fatima Blue and Gold |
| 65. | | 12 | Jonathan Krygiel | 21:34.3 | MO | Sullivan | Oct 31
| MSHSAA Class 4, 5 District 2 - Sullivan |
| 66. | | 11 | Christian Means | 21:35.2 | MO | Hermann | Oct 6
| Hermann Invitational |
| 67. | | 9 | Kyle Cudney | 21:35.6PR | MO | Union | Oct 6
| Hermann Invitational |
| 68. | | 12 | Zach Deardeuff | 21:39.4PR | MO | St. James | Oct 13
| Owensville HS Invitational |
| 69. | | 9 | Aidan Heaney | 21:44.1 | MO | Hermann | Oct 6
| Hermann Invitational |
| 70. | | 10 | Brent Miller | 22:06.8 | MO | St. Clair | Sep 24
| Belle Invitational |
| 71. | | 10 | Samuel Nicks | 22:10.2 | MO | Owensville | Sep 24
| Belle Invitational |
| 72. | | 9 | Trenton Million | 22:12.1PR | MO | Owensville | Sep 19
| Bismarck Invitational |
| 73. | | 9 | Cole Cudney | 22:18.1PR | MO | Union | Oct 6
| Hermann Invitational |
| 74. | | 10 | Michael Owens | 22:20.9 | MO | Pacific | Oct 6
| Hermann Invitational |
| 75. | | 9 | George Bonney | 22:22.7PR | MO | Sullivan | Oct 13
| Owensville HS Invitational |
| 76. | | 11 | Ryan Bozada | 22:30.7PR | MO | St. Clair | Oct 24
| Fatima Blue and Gold |
| 77. | | 9 | Jayden Barnett | 22:47.0 | MO | Owensville | Oct 6
| Hermann Invitational |
| 78. | | 10 | Walker Hardy | 22:52.0 | MO | Sullivan | Sep 26
| Gans Creek Classic |
| 79. | | 10 | David Otten | 22:56.9 | MO | New Haven | Oct 31
| MSHSAA Class 2 District 4 - Linn |
| 80. | | 9 | Palmer Wade | 22:58.9 | MO | Pacific | Oct 10
| Potosi Invitational/MAAA Conference |
| 81. | | 10 | Tristan Rodrigue | 23:06.1 | MO | St. Clair | Sep 24
| Belle Invitational |
| 82. | | 11 | Alex Reinwald | 23:10.4 | MO | St. Clair | Sep 24
| Belle Invitational |
| 83. | | 11 | Samuel Hoffman | 23:16.2 | MO | Owensville | Sep 24
| Belle Invitational |
| 84. | | 9 | Andrew Blankenship | 23:21.2 | MO | Owensville | Oct 6
| Hermann Invitational |
| 85. | | 11 | Michael Aehle | 23:34.0 | MO | Pacific | Oct 13
| Owensville HS Invitational |
| 86. | | 9 | John Borzillo | 24:08.2 | MO | Hermann | Sep 24
| Belle Invitational |
| 87. | | 12 | Dalton Rehmert | 24:15.6 | MO | Hermann | Sep 24
| Belle Invitational |
| 88. | | 10 | Dakota Phegley | 24:17.7 | MO | Sullivan | Oct 6
| Hermann Invitational |
| 89. | | 12 | Hunter Foree | 24:40.4PR | MO | Hermann | Oct 6
| Hermann Invitational |
| 90. | | 9 | Jim Jenkins | 24:44.4 | MO | Owensville | Oct 6
| Hermann Invitational |
| 91. | | 12 | Tony Kingston | 24:59.0 | MO | St. Clair | Sep 24
| Belle Invitational |
| 92. | | 12 | Kenneth Brown | 25:28.4 | MO | St. Clair | Oct 13
| Owensville HS Invitational |
| 93. | | 9 | Jonathan Zapolski | 25:50.4PR | MO | Pacific | Oct 6
| Hermann Invitational |
| 94. | | 9 | Ian Studdard | 25:59.5 | MO | Sullivan | Oct 6
| Hermann Invitational |
| 95. | | 10 | Ryan Trentmann | 26:33.6 | MO | St. Clair | Sep 24
| Belle Invitational |
| 96. | | 12 | Josh Kleinheider | 26:41.7 | MO | New Haven | Oct 6
| Hermann Invitational |
| 97. | | 11 | Trevor Wilson | 27:18.9 | MO | St. James | Sep 17
| Steelville MS/HS Invitational |
| 98. | | 9 | Christian Hulsey | 27:19.0PR | MO | Sullivan | Oct 20
| Four Rivers Conference Meet |
| 99. | | 9 | Sebastian Means | 27:32.1PR | MO | Hermann | Oct 6
| Hermann Invitational |
| 100. | | 11 | Gavin Allen | 28:14.9PR | MO | New Haven | Oct 17
| 2020 Hancock Invitational |