| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | | 11 | Mason Hoover | 15:46.1PR | MD | Chopticon | Nov 4
| MPSSAA 3A South Region Championships |
| 2. | | 10 | Peter Imhof | 16:23.3 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 3. | 17 | 11 | Bryce Dufrene | 17:03.3 | MD | Chopticon | Oct 20
| 2021 SMAC Cross Country Championship |
| 4. | | 12 | John Owens | 17:04.7PR | MD | Chopticon | Oct 20
| 2021 SMAC Cross Country Championship |
| 5. | | 12 | Alexander Seskar | 17:11.9PR | MD | Great Mills | Nov 4
| MPSSAA 3A South Region Championships |
| 6. | | 10 | Dominic Longobardi | 17:16.2 | MD | Chopticon | Nov 4
| MPSSAA 3A South Region Championships |
| 7. | | 10 | James Owens | 17:16.8PR | MD | Chopticon | Nov 4
| MPSSAA 3A South Region Championships |
| 8. | | 10 | Ryan Ledig | 17:21.2 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 9. | | 12 | Andrew Sukhram | 17:23.4PR | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 10. | | 10 | Grant Pritchard | 17:32.5 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 11. | -2 | 10 | Nick Watson | 17:33.0 | MD | Chopticon | Nov 4
| MPSSAA 3A South Region Championships |
| 12. | 15 | 9 | Braden Gutekunst | 17:33.1 | MD | Great Mills | Nov 4
| MPSSAA 3A South Region Championships |
| 13. | 15 | 10 | Weston Carr | 17:51.3 | MD | Chopticon | Oct 20
| 2021 SMAC Cross Country Championship |
| 14. | | 11 | Blake Butler | 17:55.2PR | MD | Chopticon | Nov 4
| MPSSAA 3A South Region Championships |
| 15. | | 11 | Brayden Fogel | 18:00.8PR | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 16. | | 11 | Will Cassetta | 18:04.2PR | MD | Leonardtown | Oct 20
| 2021 SMAC Cross Country Championship |
| 17. | | 9 | Kody Clarke | 18:10.6 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 18. | | 12 | Chris Salter | 18:24.6PR | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 19. | | 10 | Brendan Nutter | 18:24.7 | MD | Chopticon | Oct 20
| 2021 SMAC Cross Country Championship |
| 20. | | 12 | Graham Salter | 18:29.4PR | MD | Leonardtown | Oct 20
| 2021 SMAC Cross Country Championship |
| 21. | | 12 | WIll Standish | 18:41.9PR | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 22. | | 9 | Foster Kirby | 18:51.5 | MD | Leonardtown | Oct 20
| 2021 SMAC Cross Country Championship |
| 23. | | 10 | Jack Kuta | 18:54.9 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 24. | | 11 | Anderson Loesch | 19:03.6 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 25. | | 11 | Ben Kurtz | 19:19.3PR | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 26. | | 10 | Konnor Kent | 19:31.5 | MD | Chopticon | Oct 20
| 2021 SMAC Cross Country Championship |
| 27. | | 9 | Robert Ross | 19:35.2 | MD | Great Mills | Nov 4
| MPSSAA 3A South Region Championships |
| 28. | | 9 | Cole Hargreaves | 19:37.7 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 29. | | 10 | Everett Grube | 19:58.9 | MD | Great Mills | Nov 4
| MPSSAA 3A South Region Championships |
| 30. | | 12 | Quron Leatherwood | 21:15.6PR | MD | Great Mills | Oct 20
| 2021 SMAC Cross Country Championship |
| 31. | | 10 | Jackson Northrup | 21:24.0PR | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 32. | | 9 | Jack Venendaal | 21:29.5 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 33. | | 11 | Trent Williams | 22:20.4 | MD | Chopticon | Sep 22
| Chopticon, Great Mills, La Plata |
| 34. | | 11 | Jeffrey Martines | 22:33.3PR | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 35. | | 9 | Andrew Salter | 22:33.8 | MD | Leonardtown | Oct 16
| Seahawk Invitational |
| 36. | | 11 | Joseph Lang | 22:42.8PR | MD | Great Mills | Nov 4
| MPSSAA 3A South Region Championships |
| 37. | 17 | 11 | Timothy Reardon | 23:15.1 | MD | Great Mills | Nov 4
| MPSSAA 3A South Region Championships |
| 38. | | 12 | Patrick Albright | 23:23.9PR | MD | Great Mills | Nov 4
| MPSSAA 3A South Region Championships |
| 39. | | 9 | Logan Dean | 24:34.5 | MD | Chopticon | Sep 22
| Chopticon, Great Mills, La Plata |
| 40. | | 12 | Aaron Gaffud | 25:13.4PR | MD | Chopticon | Sep 22
| Chopticon, Great Mills, La Plata |
| 41. | | 10 | Ryan Brown | 25:29.2 | MD | Great Mills | Oct 20
| 2021 SMAC Cross Country Championship |
| 42. | | 11 | Connor Strafella | 25:52.6 | MD | Chopticon | Sep 22
| Chopticon, Great Mills, La Plata |
| 43. | | 11 | Conner Bowser | 27:16.9PR | MD | Chopticon | Sep 22
| Chopticon, Great Mills, La Plata |
| 44. | | 11 | Trent Barbour | 27:33.2 | MD | Chopticon | Sep 22
| Chopticon, Great Mills, La Plata |
| 45. | 16 | 10 | William Hughes | 29:00.0PR | MD | Great Mills | Oct 20
| 2021 SMAC Cross Country Championship |