| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 17 | 12 | Gavin Sherry | 14:58.6PR | CT | Conard | Sep 25
| Ocean State XC Invitational |
| 2. | 17 | 12 | Callum Sherry | 15:14.7PR | CT | Conard | Sep 25
| Ocean State XC Invitational |
| 3. | 17 | 12 | Aidan Puffer | 15:25.0 | CT | Manchester | Nov 5
| CIAC State Open Championships |
| 4. | 18 | 12 | Michael Bohlke | 15:29.0PR | CT | Newington | Nov 5
| CIAC State Open Championships |
| 5. | 17 | 12 | Carver Morgan | 15:39.0PR | CT | Avon | Sep 21
| Conard, Glastonbury @ Avon |
| 6. | 17 | 12 | Justin Cascio | 15:51.5PR | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 7. | | 12 | Joseph Accurso | 15:58.0PR | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| 8. | 16 | 11 | Francis Porrini III | 15:59.0PR | CT | Bristol Central | Oct 5
| Maloney vs Bristol Central & Lewis Mills |
| 9. | 18 | 12 | Jack Martin | 16:02.0 | CT | Avon | Nov 5
| CIAC State Open Championships |
| 10. | 17 | 12 | Walker Beverly | 16:07.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 11. | 16 | 10 | Luke Davis | 16:16.0 | CT | Simsbury | Nov 5
| CIAC State Open Championships |
| 12. | 17 | 12 | Sean Barkasy | 16:17.4PR | CT | Manchester | Oct 19
| CCC Cross Country Championships |
| 13. | 17 | 12 | Davis Anderson | 16:19.0PR | CT | Simsbury | Sep 21
| Hall vs Farmington, Simsbury |
| 14. | 17 | 12 | Luke Stoeffler | 16:22.0PR | CT | Tolland | Oct 9
| 37th Wickham Park XC Invitational |
| | | 12 | Evan Boland | 16:22.0PR | CT | E.O. Smith | Nov 5
| CIAC State Open Championships |
| 16. | 17 | 12 | William Calhoun | 16:25.9PR | CT | RHAM | Sep 18
| 10th Connecticut River Valley Invitational |
| 17. | | 11 | Ryan Gagne | 16:30.0 | CT | Wethersfield | Nov 5
| CIAC State Open Championships |
| | 15 | 10 | Isaac Mahler | 16:30.0 | CT | Hall | Nov 5
| CIAC State Open Championships |
| 19. | 17 | 12 | Grayson Borla | 16:32.0PR | CT | Southington | Oct 12
| Southington at NW Catholic |
| 20. | 17 | 11 | Avery Allen | 16:36.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 21. | 16 | 11 | Nathaniel Aronson | 16:39.0 | CT | Hall | Nov 19
| Run Rabbit Run 2021 |
| 22. | 17 | 11 | Jake Nafis | 16:48.0 | CT | Southington | Oct 12
| Southington at NW Catholic |
| 23. | | 11 | Brayden Bayek | 16:50.0 | CT | Rocky Hill | Nov 5
| CIAC State Open Championships |
| 24. | 18 | 12 | Lucas Hester | 16:56.0PR | CT | Avon | Oct 5
| Hall vs Avon, NW Catholic |
| | 16 | 11 | Colin Goldschmidt | 16:56.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 26. | | 12 | Jack O'Donnell | 16:58.0PR | CT | Avon | Sep 21
| Conard, Glastonbury @ Avon |
| | | 12 | Joshua Burr | 16:58.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| | | 12 | Liam Scully | 16:58.0PR | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 29. | | 11 | Noah Burgio | 17:02.0PR | CT | Conard | Sep 21
| Conard, Glastonbury @ Avon |
| 30. | 16 | 11 | Ethan Striff-Cave | 17:03.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 31. | 16 | 10 | Jameson Sederquist | 17:07.3PR | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 32. | | 12 | Nicholas Bailey | 17:08.0PR | CT | Avon | Oct 12
| Farmington @ Avon |
| 33. | | 11 | Apurv Manjreker | 17:09.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 34. | 15 | 10 | Jack Mattingly | 17:09.9 | CT | E.O. Smith | Sep 18
| 10th Connecticut River Valley Invitational |
| 35. | 17 | 12 | Lucas Thompson | 17:11.0PR | CT | Simsbury | Sep 21
| Hall vs Farmington, Simsbury |
| 36. | 16 | 11 | Lucas Pyrro | 17:12.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 37. | 18 | 11 | Ben Fisher | 17:12.9PR | CT | Berlin | Sep 25
| 9th Winding Trails XC Invitational |
| 38. | 17 | 12 | Israel Caro | 17:13.4PR | CT | East Catholic | Oct 1
| 9th Harry Geraghty XC Invite |
| 39. | | 10 | Troy Miller | 17:13.8 | CT | RHAM | Sep 18
| 10th Connecticut River Valley Invitational |
| 40. | | 12 | Bryan Martinez | 17:14.0PR | CT | Rocky Hill | Nov 5
| CIAC State Open Championships |
| 41. | | 11 | Harrison (William) ... | 17:15.0 | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| 42. | | 12 | Kevin Graziosi | 17:16.0PR | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| | | 11 | Thomas Armistead | 17:16.0 | CT | Avon | Nov 5
| CIAC State Open Championships |
| 44. | | 12 | Cody Stone | 17:24.0PR | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| 45. | | 11 | Jacob Robinson-Smey | 17:24.9 | CT | E.O. Smith | Sep 18
| 10th Connecticut River Valley Invitational |
| 46. | | 12 | Logan Crowley | 17:27.0PR | CT | Bristol Eastern | Sep 21
| BE-Berlin @Lewis Mills |
| 47. | | 12 | Jamie Rendon | 17:28.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 48. | 17 | 11 | Drew Nafis | 17:29.0 | CT | Southington | Nov 5
| CIAC State Open Championships |
| 49. | | 11 | Uri Noyman | 17:31.0 | CT | Hall | Oct 12
| Conard vs Hall |
| 50. | | 12 | Jevonte Eaves | 17:33.0 | CT | Avon | Oct 12
| Farmington @ Avon |
| 51. | | 12 | Liam McGoldrick | 17:34.0PR | CT | Simsbury | Nov 5
| CIAC State Open Championships |
| 52. | 16 | 10 | Zachary Barth | 17:35.8 | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 53. | 15 | 9 | William Lancaster | 17:38.0 | CT | Avon | Oct 5
| Hall vs Avon, NW Catholic |
| 54. | | 12 | Caleb Curtis | 17:39.0PR | CT | Manchester | Nov 5
| CIAC State Open Championships |
| 55. | | 11 | Christopher Roy | 17:39.4 | CT | Bristol Central | Oct 1
| 9th Harry Geraghty XC Invite |
| 56. | 17 | 12 | Logan Miceli | 17:40.0PR | CT | Southington | Oct 12
| Southington at NW Catholic |
| 57. | | 12 | Brendan Kelly | 17:43.5 | CT | Farmington | Sep 25
| 9th Winding Trails XC Invitational |
| 58. | 16 | 10 | Jonathan York | 17:44.0PR | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 59. | | 10 | Francis Dewander | 17:45.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 60. | 14 | 12 | Jack Curry | 17:50.0PR | CT | Maloney | Oct 5
| Maloney vs Bristol Central & Lewis Mills |
| | | 10 | Colby Bornstein | 17:50.0 | CT | Tolland | Oct 9
| 37th Wickham Park XC Invitational |
| | 18 | 12 | Sean McDaniel | 17:50.0PR | CT | Hall | Oct 12
| Conard vs Hall |
| 63. | | 12 | Matthew Enright | 17:50.6PR | CT | E.O. Smith | Sep 18
| 10th Connecticut River Valley Invitational |
| 64. | | 12 | Nicolas Martin | 17:51.0 | CT | Conard | Oct 12
| Conard vs Hall |
| 65. | 17 | 12 | Samuel Aronow | 17:52.0 | CT | Hall | Oct 12
| Conard vs Hall |
| 66. | | 12 | Nicholas Peterson | 17:53.0PR | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 67. | | 12 | Brendan Leone | 17:54.0PR | CT | Southington | Oct 12
| Southington at NW Catholic |
| 68. | 15 | 10 | Apollo Josephson | 17:55.5PR | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 69. | | 10 | Chase McNamara | 17:56.0 | CT | Plainville | Oct 9
| 37th Wickham Park XC Invitational |
| 70. | | 10 | Gabriel Montoya | 17:57.6 | CT | E.O. Smith | Sep 18
| 10th Connecticut River Valley Invitational |
| 71. | | 11 | Ford Gillespie | 17:58.0PR | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 72. | | 11 | Dominic Pena | 17:58.4 | CT | Glastonbury | Sep 28
| Farmington vs Glastonbury & North West Cathol... |
| | | 10 | Troy Giaccone | 17:58.4PR | CT | Glastonbury | Oct 1
| 9th Harry Geraghty XC Invite |
| 74. | 17 | 12 | Cole Smith | 17:59.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| | 16 | 10 | Evan Piccioli | 17:59.0 | CT | Conard | Oct 5
| Conard vs Farmington, Southington |
| 76. | | 11 | Dominic Tartarelli | 18:02.0 | CT | Bristol Eastern | Sep 21
| BE-Berlin @Lewis Mills |
| | 16 | 10 | Christopher Regalbu... | 18:02.0 | CT | Southington | Oct 12
| Southington at NW Catholic |
| 78. | | 9 | Benjamin Lewis | 18:03.0 | CT | Hall | Oct 12
| Conard vs Hall |
| 79. | | 11 | Cameron Colletti | 18:03.3 | CT | Glastonbury | Oct 1
| 9th Harry Geraghty XC Invite |
| 80. | | 12 | Matthew Sampt | 18:05.0 | CT | Conard | Sep 21
| Conard, Glastonbury @ Avon |
| | | 12 | Rowan Gottshall | 18:05.0PR | CT | Simsbury | Sep 21
| Hall vs Farmington, Simsbury |
| 82. | | 11 | Grant Walters | 18:05.1 | CT | Conard | Sep 25
| Ocean State XC Invitational |
| 83. | 17 | 12 | Abdullah Barlas | 18:07.0PR | CT | Manchester | Nov 5
| CIAC State Open Championships |
| 84. | 17 | 12 | Matthew Rostkowski | 18:07.5PR | CT | Rocky Hill | Oct 19
| CCC Cross Country Championships |
| 85. | 16 | 11 | Nicholas Atkins | 18:07.9PR | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 86. | 16 | 10 | Jonathan Pincus | 18:09.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| | | 9 | William Liebler | 18:09.0 | CT | Southington | Oct 5
| Conard vs Farmington, Southington |
| 88. | | 10 | Gabe Frazzini Kenda... | 18:12.1PR | CT | Wethersfield | Sep 18
| 10th Connecticut River Valley Invitational |
| 89. | 16 | 11 | Austin Vale da Serr... | 18:13.0PR | CT | Berlin | Sep 25
| 9th Winding Trails XC Invitational |
| 90. | | 12 | Kyle Jennings | 18:16.0PR | CT | Simsbury | Sep 21
| Hall vs Farmington, Simsbury |
| | | 12 | Jake Tacinelli | 18:16.0PR | CT | Avon | Oct 23
| Avon, Simsbury @ Southington |
| | | 12 | William McCoy | 18:16.0PR | CT | Manchester | Nov 1
| CIAC Division LL Championships |
| 93. | | 12 | Will McCoy | 18:16.6PR | CT | Manchester | Oct 19
| CCC Cross Country Championships |
| 94. | 15 | 10 | Sean Morley | 18:17.0 | CT | Conard | Sep 21
| Conard, Glastonbury @ Avon |
| 95. | | 12 | Liam Stec | 18:19.6 | CT | Wethersfield | Sep 18
| 10th Connecticut River Valley Invitational |
| 96. | | 10 | Valiantsin Kasabruk... | 18:20.5 | CT | Plainville | Oct 19
| CCC Cross Country Championships |
| 97. | 16 | 11 | Joshua Mazar | 18:21.5PR | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 98. | 16 | 11 | Ryan Heneghan | 18:23.0 | CT | RHAM | Sep 18
| 10th Connecticut River Valley Invitational |
| | | 10 | Rocco Pizzitola | 18:23.0 | CT | Southington | Oct 12
| Southington at NW Catholic |
| | | 9 | Charles Lasko | 18:23.0 | CT | Plainville | Nov 1
| CIAC Division M Championships |
Men
Women