| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 18 | 12 | Alex Xavier | 15:34.4PR | MD | Fallston | Oct 12
| Chesapeake Championships |
| 2. | | 12 | Day Leone | 15:47.3PR | MD | Bohemia Manor | Oct 12
| Chesapeake Championships |
| 3. | | 12 | John Condon | 15:55.5PR | MD | Cambridge South Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 4. | 17 | 12 | Quinn Daly | 16:28.4PR | MD | Fallston | Oct 12
| Chesapeake Championships |
| 5. | 17 | 12 | Bryce Kahler | 16:33.0PR | MD | Fallston | Oct 12
| Chesapeake Championships |
| 6. | | 12 | Samuel Dickerson | 16:53.1PR | MD | Bohemia Manor | Oct 12
| Chesapeake Championships |
| 7. | 16 | 11 | Seth Barron | 17:12.1 | MD | Snow Hill | Oct 27
| 2021 Bayside XC Championships |
| 8. | | 12 | Noah Beck | 17:25.8PR | MD | Bohemia Manor | Oct 12
| Chesapeake Championships |
| 9. | | 12 | Berkeley Tisch | 17:28.0 | MD | Patterson Mill | Sep 28
| Harford Invite |
| 10. | | 12 | Chandler Wilson | 17:43.0PR | MD | Patterson Mill | Sep 28
| Harford Invite |
| 11. | 17 | 11 | Antonio Hernandez | 17:44.0 | MD | Fallston | Sep 28
| Harford Invite |
| 12. | | 12 | Casin Brown | 17:50.3PR | MD | Bohemia Manor | Oct 12
| Chesapeake Championships |
| 13. | | 12 | Diego Gonzalez | 17:58.0PR | MD | Patterson Mill | Sep 28
| Harford Invite |
| 14. | 15 | 10 | Logan Hurney | 17:58.3 | MD | Snow Hill | Oct 27
| 2021 Bayside XC Championships |
| 15. | | 9 | Eryk Bender | 18:03.8 | MD | Fallston | Oct 12
| Chesapeake Championships |
| 16. | | 10 | Brian McCurdy | 18:03.9PR | MD | Fallston | Oct 12
| Chesapeake Championships |
| 17. | | 11 | Nasir Polk | 18:12.2 | MD | North Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 18. | | 12 | Evan Payne | 18:14.2PR | MD | Cambridge South Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 19. | 16 | 11 | Ja'Naz Crawley | 18:19.6PR | MD | Snow Hill | Oct 27
| 2021 Bayside XC Championships |
| 20. | | 9 | Alex McMillan | 18:41.0PR | MD | Bohemia Manor | Sep 21
| CMW, Fallston, Bo Manor |
| 21. | | 10 | Evan Wakefield | 18:43.5 | MD | Bohemia Manor | Oct 12
| Chesapeake Championships |
| 22. | | 9 | Jackson Hunsinger | 18:45.6 | MD | Fallston | Oct 12
| Chesapeake Championships |
| 23. | | 12 | Ian Davis | 18:46.9 | MD | Bohemia Manor | Oct 12
| Chesapeake Championships |
| 24. | | 10 | Grayson Kasten | 18:52.0 | MD | Fallston | Oct 12
| Chesapeake Championships |
| 25. | | 12 | Tradd Cooper | 18:59.6PR | MD | Mardela | Oct 27
| 2021 Bayside XC Championships |
| 26. | 16 | 11 | Jacob Bohle | 18:59.7PR | MD | Kent County | Oct 27
| 2021 Bayside XC Championships |
| 27. | | 12 | Anthony Czerwinski | 19:05.5PR | MD | Bohemia Manor | Oct 12
| Chesapeake Championships |
| 28. | | 12 | Addison Smith | 19:06.0PR | MD | Cambridge South Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 29. | | 12 | Cameron Dunne | 19:11.0 | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 30. | | 12 | Andrew Gneo | 19:13.0PR | MD | Patterson Mill | Sep 28
| Harford Invite |
| 31. | | 10 | Steven Lewis | 19:15.0PR | MD | Fallston | Oct 12
| Chesapeake Championships |
| 32. | | 12 | Thomas Reincke | 19:21.7PR | MD | North Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 33. | | 10 | Alex Chacona | 19:22.0PR | MD | Fallston | Oct 12
| Chesapeake Championships |
| 34. | | 12 | Rager Laughlin | 19:28.0PR | MD | Patterson Mill | Sep 28
| Harford Invite |
| 35. | | 10 | Gavin Kahler | 19:36.0 | MD | Fallston | Oct 12
| Chesapeake Championships |
| 36. | 18 | 12 | Diontraye Bratten | 19:36.6PR | MD | Snow Hill | Oct 27
| 2021 Bayside XC Championships |
| 37. | 14 | 9 | Jack Corea | 19:44.0PR | MD | Fallston | Oct 12
| Chesapeake Championships |
| 38. | | 10 | Tyler Vandarwarka | 19:46.8 | MD | Havre De Grace | Sep 21
| HdG, Harford Tech, Aberdeen @ HDG |
| 39. | 15 | 10 | Kyle Fellon | 19:49.7 | MD | North Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 40. | | 11 | Michael Young | 19:51.5 | MD | Perryville | Nov 13
| MPSSAA 1A State Championships |
| 41. | | 10 | Ian Rapp | 19:56.0 | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 42. | | 11 | Gavin Litton | 19:57.9PR | MD | Pocomoke | Oct 27
| 2021 Bayside XC Championships |
| 43. | | 11 | Alex Chacona | 20:05.0PR | MD | Fallston | Sep 28
| Harford Invite |
| 44. | 16 | 11 | Justin Hurney | 20:12.2 | MD | Snow Hill | Sep 9
| VI Annual Rumble in the Jungle |
| 45. | | 11 | Declan Clayton | 20:25.0 | MD | Cambridge South Dorchester | Sep 9
| VI Annual Rumble in the Jungle |
| 46. | | 11 | Nathan Hillhouse | 20:29.2PR | MD | Patterson Mill | Nov 13
| MPSSAA 1A State Championships |
| 47. | | 9 | Luca Cangelosi | 20:34.0PR | MD | Fallston | Sep 28
| Harford Invite |
| 48. | 15 | 10 | Matthew Elliott | 20:36.0 | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 49. | | 11 | Preston Dalling | 20:40.0PR | MD | Patterson Mill | Sep 28
| Harford Invite |
| 50. | | 9 | Braeden Walker | 20:43.8PR | MD | Perryville | Sep 21
| Edgewood, Joppatowne @ Perryville |
| 51. | 18 | 12 | Matt Grahe | 20:45.7 | MD | Perryville | Sep 21
| Edgewood, Joppatowne @ Perryville |
| 52. | | 10 | Ben Loller | 20:48.0PR | MD | Kent County | Oct 27
| 2021 Bayside XC Championships |
| 53. | | 10 | Andrew Higgins | 20:53.1 | MD | Havre De Grace | Oct 19
| CMW, Rising Sun, Havre de Grace |
| 54. | | 11 | Leighton Dell | 21:03.0 | MD | Bohemia Manor | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 55. | | 11 | Kent Bromley | 21:07.5PR | MD | Havre De Grace | Sep 21
| HdG, Harford Tech, Aberdeen @ HDG |
| 56. | | 12 | Luke Dean | 21:18.5PR | MD | Mardela | Oct 27
| 2021 Bayside XC Championships |
| 57. | 16 | 10 | Andrew Grosso | 21:19.4 | MD | Patterson Mill | Sep 21
| Rising Sun, Patterson Mill at Bel Air (702 N ... |
| 58. | | 12 | Ryan Baker | 21:24.0PR | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 59. | | 9 | Eric Cumbie | 21:28.9 | MD | Havre De Grace | Oct 19
| CMW, Rising Sun, Havre de Grace |
| 60. | | 12 | Joseph Amaral | 21:38.0PR | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 61. | | 10 | Ethan Dell | 21:42.0 | MD | Bohemia Manor | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 62. | | 9 | Robert Heinzelman | 21:44.0 | MD | Bohemia Manor | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 63. | | 11 | Steven Hunt | 21:45.7 | MD | Crisfield | Oct 27
| 2021 Bayside XC Championships |
| 64. | | 11 | Owen Fabian | 21:48.7PR | MD | Bohemia Manor | Sep 14
| Aberdeen, Bel Air, Bohemia Manor @ North East |
| 65. | | 9 | DaJon Harris | 22:05.3 | MD | Cambridge South Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 66. | | 10 | Jacob Fruchey | 22:11.2 | MD | Havre De Grace | Oct 19
| CMW, Rising Sun, Havre de Grace |
| 67. | 17 | 12 | Raymond Chen | 22:12.9 | MD | Pocomoke | Oct 27
| 2021 Bayside XC Championships |
| 68. | | 12 | Amar Hathiramani | 22:15.0PR | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 69. | | 12 | Jean Nieto | 22:21.0PR | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 70. | | 12 | Sam Buckel | 22:23.6 | MD | Kent County | Oct 27
| 2021 Bayside XC Championships |
| 71. | | 10 | Matthew Dubois | 22:24.0 | MD | Fallston | Sep 21
| CMW, Fallston, Bo Manor |
| 72. | | 12 | Andrew Trinh | 22:32.0PR | MD | Patterson Mill | Sep 28
| Harford Invite |
| | | 11 | Mason Darsney | 22:32.0 | MD | Bohemia Manor | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 74. | | 9 | Mason Green | 22:33.0 | MD | Mardela | Oct 27
| 2021 Bayside XC Championships |
| 75. | | 9 | Christian Sanders | 22:38.5 | MD | Cambridge South Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 76. | | 12 | Jacob Payne | 22:46.8PR | MD | Pocomoke | Oct 27
| 2021 Bayside XC Championships |
| 77. | | 12 | Gavin Dennis | 22:46.9PR | MD | Pocomoke | Oct 27
| 2021 Bayside XC Championships |
| 78. | 16 | 11 | Lucas Bruns | 23:11.3PR | MD | Joppatowne | Sep 21
| Edgewood, Joppatowne @ Perryville |
| 79. | | 9 | Philip Tran | 23:12.0PR | MD | Patterson Mill | Sep 28
| Harford Invite |
| 80. | | 12 | Gabe Carter | 23:12.8 | MD | Mardela | Oct 27
| 2021 Bayside XC Championships |
| 81. | | 9 | Daniel Racine | 23:13.1PR | MD | Bohemia Manor | Sep 14
| Aberdeen, Bel Air, Bohemia Manor @ North East |
| 82. | | 11 | RIley Vaugn | 23:35.0PR | MD | Fallston | Sep 21
| CMW, Fallston, Bo Manor |
| 83. | | 10 | John Hubbard | 23:40.9 | MD | North Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 84. | | 12 | Rafe Adams | 23:42.1 | MD | Perryville | Sep 21
| Edgewood, Joppatowne @ Perryville |
| 85. | | 9 | Jayden Taylor | 23:43.2PR | MD | Bohemia Manor | Sep 14
| Aberdeen, Bel Air, Bohemia Manor @ North East |
| 86. | | 12 | Zackary Jarrell | 23:45.0PR | MD | Bohemia Manor | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 87. | | 9 | Josiah Harris | 23:45.7 | MD | Cambridge South Dorchester | Sep 9
| VI Annual Rumble in the Jungle |
| 88. | | 12 | Caleb Norfolk | 24:08.9PR | MD | Pocomoke | Oct 27
| 2021 Bayside XC Championships |
| 89. | | 12 | Lucas Murphy | 24:22.5PR | MD | North Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 90. | 15 | 10 | Aiden Clayton | 24:24.5PR | MD | Pocomoke | Oct 27
| 2021 Bayside XC Championships |
| 91. | | 10 | Zach Adams | 24:27.6 | MD | North Dorchester | Oct 27
| 2021 Bayside XC Championships |
| 92. | | 10 | Eddie Johnson | 24:37.0 | MD | Crisfield | Oct 27
| 2021 Bayside XC Championships |
| 93. | | 12 | Nicholas May | 24:43.0 | MD | Patterson Mill | Oct 19
| Harford Tech/Bo Manor @Patterson Mill |
| 94. | | 12 | Michael Kelly | 24:43.5 | MD | Perryville | Sep 21
| Edgewood, Joppatowne @ Perryville |
| 95. | | 10 | Avery Krantz | 24:44.0 | MD | Fallston | Oct 12
| Chesapeake Championships |
| 96. | 15 | 10 | James Sills | 24:44.7 | MD | Snow Hill | Oct 27
| 2021 Bayside XC Championships |
| 97. | | 12 | Gabe Phillips | 25:06.8PR | MD | Perryville | Sep 21
| Edgewood, Joppatowne @ Perryville |
| 98. | | 11 | Giovanni Caruso | 25:12.9 | MD | Pocomoke | Oct 27
| 2021 Bayside XC Championships |
| 99. | 18 | 12 | Ian Portell | 25:13.4PR | MD | Snow Hill | Oct 27
| 2021 Bayside XC Championships |
| 100. | | 12 | Destin Green | 25:21.5 | MD | Cambridge South Dorchester | Oct 27
| 2021 Bayside XC Championships |