| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 17 | 12 | Aidan Puffer | 15:25.0 | CT | Manchester | Nov 5
| CIAC State Open Championships |
| 2. | | 12 | Joseph Accurso | 15:58.0PR | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| 3. | 17 | 12 | Nikita Omelchenko | 16:05.0PR | CT | Wilbur Cross | Nov 5
| CIAC State Open Championships |
| 4. | 17 | 12 | Walker Beverly | 16:07.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 5. | 15 | 10 | Steven Hergenrother | 16:13.0 | CT | Ridgefield | Nov 5
| CIAC State Open Championships |
| 6. | 17 | 12 | Matthew McDonough | 16:15.0PR | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| | | 12 | Zachary Taubman | 16:15.0 | CT | Staples | Oct 20
| FCIAC XC Championships |
| 8. | | 12 | Mason Beaudette | 16:16.0PR | CT | Amity | Nov 5
| CIAC State Open Championships |
| 9. | 17 | 12 | Sean Barkasy | 16:17.4PR | CT | Manchester | Oct 19
| CCC Cross Country Championships |
| 10. | | 12 | Mohammed Abunar | 16:20.0PR | CT | Trumbull | Oct 20
| FCIAC XC Championships |
| 11. | | 12 | Jack Dovaras | 16:22.0PR | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| 12. | 15 | 10 | Devon Rosemark | 16:23.4PR | CT | Danbury Hatters HCYS Track & XC Club | Nov 14
| USATF Connecticut Association Junior Olympic ... |
| 13. | 15 | 10 | Isaac Mahler | 16:30.0 | CT | Hall | Nov 5
| CIAC State Open Championships |
| 14. | 17 | 12 | Jalen St.Fort | 16:31.0PR | CT | Staples | Oct 20
| FCIAC XC Championships |
| 15. | 17 | 12 | Grayson Borla | 16:32.0PR | CT | Southington | Oct 12
| Southington at NW Catholic |
| | | 12 | Benjamin Mickool | 16:32.0 | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| 17. | 17 | 11 | Avery Allen | 16:36.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 18. | | 12 | Joseph Callanan | 16:38.0PR | CT | Fairfield Warde | Oct 20
| FCIAC XC Championships |
| | | 12 | Parker Paragas | 16:38.0PR | CT | Amity | Nov 5
| CIAC State Open Championships |
| 20. | 18 | 12 | Zachary Jelinek | 16:39.0PR | CT | Greenwich | Oct 20
| FCIAC XC Championships |
| | 16 | 11 | Nathaniel Aronson | 16:39.0 | CT | Hall | Nov 19
| Run Rabbit Run 2021 |
| 22. | | 12 | Bronson Vo | 16:46.0PR | CT | Trumbull | Oct 20
| FCIAC XC Championships |
| 23. | | 12 | Angel Perez | 16:48.0PR | CT | Fairfield Prep | Sep 14
| Lauralton Hall/F.Prep, Amity, Branford @Foran |
| | 17 | 11 | Jake Nafis | 16:48.0 | CT | Southington | Oct 12
| Southington at NW Catholic |
| | | 12 | Henri Vieltojarvi | 16:48.0PR | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| 26. | 16 | 10 | Benjamin Lorenz | 16:50.0 | CT | Staples | Oct 20
| FCIAC XC Championships |
| 27. | 16 | 11 | Ethan Manfredi | 16:52.6PR | CT | Norwich Free Academy | Sep 25
| Ocean State XC Invitational |
| 28. | 15 | 10 | Christian Zawislack | 16:53.0 | CT | Greenwich | Oct 20
| FCIAC XC Championships |
| 29. | 16 | 11 | Colin Goldschmidt | 16:56.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 30. | | 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 |
| 32. | 16 | 11 | Ethan Striff-Cave | 17:03.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| | 15 | 10 | Parker Broderick | 17:03.0 | CT | Fairfield Warde | Oct 9
| 37th Wickham Park XC Invitational |
| 34. | | 12 | William Rodrigues | 17:04.0PR | CT | Shelton | Nov 5
| CIAC State Open Championships |
| 35. | 15 | 10 | David Carillo | 17:07.1 | CT | Trumbull | Sep 29
| Trumbull/Ridgefield/Danbury at New Canaan |
| 36. | | 12 | Alex Harrington | 17:08.4 | CT | Staples | Sep 29
| Greenwich/McMahon/Ludlowe at Staples |
| 37. | | 11 | Apurv Manjreker | 17:09.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 38. | | 12 | Tyler Crabb | 17:11.0PR | CT | Norwich Free Academy | Oct 9
| 37th Wickham Park XC Invitational |
| | 17 | 12 | Ryan Scappaticci | 17:11.0PR | CT | Danbury | Oct 20
| FCIAC XC Championships |
| 40. | 16 | 11 | Lucas Pyrro | 17:12.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 41. | 17 | 12 | Griffin Blood | 17:13.0PR | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| 42. | | 11 | Harrison (William) ... | 17:15.0 | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| 43. | | 12 | Kevin Graziosi | 17:16.0PR | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| | | 12 | Rory Tarsy | 17:16.0 | CT | Staples | Nov 5
| CIAC State Open Championships |
| 45. | | 12 | Noah Robison | 17:17.0PR | CT | Staples | Nov 5
| CIAC State Open Championships |
| 46. | | 12 | Cody Stone | 17:24.0PR | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| 47. | | 11 | James Cunningham IV | 17:26.0 | CT | Fairfield Warde | Oct 20
| FCIAC XC Championships |
| 48. | 17 | 12 | Steven Confesor-Cha... | 17:26.9PR | CT | Danbury | Sep 25
| Ocean State XC Invitational |
| 49. | | 11 | Luke Pacheco | 17:27.0PR | CT | Shelton | Nov 5
| CIAC State Open Championships |
| 50. | | 12 | Jamie Rendon | 17:28.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| | | 12 | Quinn Collins | 17:28.0PR | CT | Greenwich | Oct 20
| FCIAC XC Championships |
| 52. | 16 | 11 | Liam Edson | 17:29.0 | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| | 17 | 11 | Drew Nafis | 17:29.0 | CT | Southington | Nov 5
| CIAC State Open Championships |
| 54. | 16 | 11 | Daniel Goldberg | 17:30.0 | CT | Westhill (CT) | Oct 20
| FCIAC XC Championships |
| 55. | | 12 | Kyle Harrington | 17:30.8 | CT | Staples | Sep 29
| Greenwich/McMahon/Ludlowe at Staples |
| 56. | 15 | 9 | Sebastian Halpern | 17:31.0 | CT | Wilbur Cross | Oct 9
| 37th Wickham Park XC Invitational |
| | | 11 | Uri Noyman | 17:31.0 | CT | Hall | Oct 12
| Conard vs Hall |
| | | 12 | George Kocadag | 17:31.0PR | CT | Staples | Oct 20
| FCIAC XC Championships |
| 59. | | 11 | Matthew Fleming | 17:32.0 | CT | Staples | Oct 9
| 37th Wickham Park XC Invitational |
| 60. | | 10 | Charles Williamson | 17:35.0 | CT | Fairfield Warde | Oct 20
| FCIAC XC Championships |
| 61. | 17 | 12 | Christopher Twombly | 17:35.6PR | CT | Danbury | Sep 25
| Ocean State XC Invitational |
| 62. | | 12 | Varujan Edwards | 17:38.7 | CT | Trumbull | Sep 29
| Trumbull/Ridgefield/Danbury at New Canaan |
| 63. | | 11 | Tyler Kocadag | 17:39.0 | CT | Staples | Oct 20
| FCIAC XC Championships |
| | | 12 | Caleb Curtis | 17:39.0PR | CT | Manchester | Nov 5
| CIAC State Open Championships |
| 65. | | 12 | Ben Martin | 17:39.3PR | CT | Fairfield Warde | Sep 25
| Ocean State XC Invitational |
| 66. | 17 | 12 | Logan Miceli | 17:40.0PR | CT | Southington | Oct 12
| Southington at NW Catholic |
| 67. | 18 | 12 | Brodey Lu | 17:40.7PR | CT | Amity | Sep 21
| Amity Duals |
| 68. | | 12 | Ryan Donovan | 17:42.7 | CT | Ridgefield | Sep 29
| Trumbull/Ridgefield/Danbury at New Canaan |
| 69. | | 12 | Rodriguez Sebastian | 17:43.0PR | CT | Fairfield Warde | Oct 20
| FCIAC XC Championships |
| | | 12 | Jeremy Aprea | 17:43.0PR | CT | Shelton | Nov 5
| CIAC State Open Championships |
| 71. | 16 | 10 | Jonathan York | 17:44.0PR | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 72. | | 10 | Francis Dewander | 17:45.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 73. | | 12 | Troy Gromley | 17:46.0PR | CT | Trumbull | Oct 20
| FCIAC XC Championships |
| | 17 | 12 | Wolf Boone | 17:46.0PR | CT | Wilbur Cross | Nov 5
| CIAC State Open Championships |
| 75. | 18 | 12 | Sean McDaniel | 17:50.0PR | CT | Hall | Oct 12
| Conard vs Hall |
| 76. | 17 | 12 | Samuel Aronow | 17:52.0 | CT | Hall | Oct 12
| Conard vs Hall |
| 77. | | 12 | Nicholas Peterson | 17:53.0PR | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| 78. | | 12 | Brendan Leone | 17:54.0PR | CT | Southington | Oct 12
| Southington at NW Catholic |
| 79. | | 11 | David King | 17:55.0 | CT | Danbury | Oct 20
| FCIAC XC Championships |
| 80. | | 11 | Jayden Opper | 17:56.0 | CT | Shelton | Oct 9
| 37th Wickham Park XC Invitational |
| 81. | 17 | 12 | Hector Meza Sanchez | 17:57.0PR | CT | Wilbur Cross | Oct 9
| 37th Wickham Park XC Invitational |
| 82. | | 11 | Ford Gillespie | 17:58.0PR | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| | | 11 | William Fitch | 17:58.0 | CT | Staples | Oct 20
| FCIAC XC Championships |
| 84. | | 12 | Zachary Falzone | 17:58.1PR | CT | Trumbull | Sep 29
| Trumbull/Ridgefield/Danbury at New Canaan |
| 85. | | 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 |
| 87. | 17 | 12 | Cole Smith | 17:59.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| | | 11 | Elliott Schunk | 17:59.0 | CT | Fairfield Warde | Oct 20
| FCIAC XC Championships |
| 89. | | 12 | Robert Enslein | 18:00.0 | CT | Greenwich | Oct 20
| FCIAC XC Championships |
| 90. | 17 | 12 | Aidan Budge | 18:01.8PR | CT | Newtown | Sep 25
| 9th Winding Trails XC Invitational |
| 91. | 16 | 10 | Christopher Regalbu... | 18:02.0 | CT | Southington | Oct 12
| Southington at NW Catholic |
| 92. | | 9 | Benjamin Lewis | 18:03.0 | CT | Hall | Oct 12
| Conard vs Hall |
| 93. | | 11 | Cameron Colletti | 18:03.3 | CT | Glastonbury | Oct 1
| 9th Harry Geraghty XC Invite |
| 94. | 17 | 12 | Abdullah Barlas | 18:07.0PR | CT | Manchester | Nov 5
| CIAC State Open Championships |
| 95. | 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 |
| 97. | | 11 | Ryan Klaiber | 18:09.6 | CT | Trumbull | Oct 12
| Trumbull/Stamford/Darien at Ludlowe |
| 98. | | 12 | James Nichol | 18:09.8PR | CT | Amity | Sep 21
| Amity Duals |
| 99. | | 11 | Justin Adorante | 18:15.2PR | CT | Trumbull | Sep 29
| Trumbull/Ridgefield/Danbury at New Canaan |
| 100. | | 12 | William McCoy | 18:16.0PR | CT | Manchester | Nov 1
| CIAC Division LL Championships |