| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 17 | 11 | Jack Ouellette | 15:32.3PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 2. | 16 | 11 | Owen Martin | 15:42.9PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 3. | 16 | 10 | Luke Cushing | 16:03.0PR | CT | Amity | Nov 6
| CIAC State Open Boys Championship |
| 4. | 17 | 12 | Nico Boyle | 16:06.7PR | CT | North Haven | Nov 11
| New England Interscholastic XC Championships |
| 5. | | 12 | Cameron Nephew | 16:07.1PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 6. | | 12 | John Larkin | 16:16.7PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 7. | | 11 | Ben Farmer | 16:36.0PR | CT | Notre Dame-West Haven | Sep 19
| ND/SHA Duals |
| 8. | | 11 | Ian Schmeelk | 16:37.0PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 9. | 16 | 11 | Connor Garrett | 16:40.5PR | CT | Hamden | Oct 18
| SCC Cross Country Championships |
| 10. | 17 | 11 | Sebastian Halpern | 16:43.1PR | CT | Wilbur Cross | Oct 18
| SCC Cross Country Championships |
| 11. | | 11 | Tyler Deme | 16:46.4PR | CT | Sheehan | Oct 18
| SCC Cross Country Championships |
| 12. | | 12 | Coleman Love | 16:46.8PR | CT | Guilford | Oct 10
| Hamden VS Career, Guilford, & Sheehan |
| 13. | 16 | 11 | Owen Jones | 16:52.0PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 14. | | 11 | Charlie Lechowicz | 16:54.1PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 15. | 17 | 12 | Daniel D'Souza | 16:55.6PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 16. | | 12 | Alex Hansen | 17:04.0 | CT | Guilford | Nov 6
| CIAC State Open Boys Championship |
| 17. | | 12 | Jack Larkin | 17:07.4PR | CT | Xavier (CT) | Sep 23
| Bowdoin Park XC Classic |
| 18. | 16 | 10 | Alexander Medina | 17:10.7PR | CT | Hamden | Oct 18
| SCC Cross Country Championships |
| 19. | | 10 | Andrew Hawk | 17:13.0PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 20. | | 12 | Tyler Caron | 17:13.2 | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 21. | | 11 | Joseph Lechowicz | 17:19.0PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 22. | | 11 | Owen Fletcher | 17:23.0PR | CT | Notre Dame-West Haven | Sep 19
| ND/SHA Duals |
| 23. | | 10 | Landon Rubano | 17:25.8PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 24. | | 11 | James Boyd | 17:26.4PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 25. | 17 | 11 | Thomas Conklin | 17:27.0PR | CT | Lyman Hall | Oct 18
| SCC Cross Country Championships |
| 26. | 17 | 12 | Jacob Fagan | 17:29.3PR | CT | Xavier (CT) | Oct 18
| SCC Cross Country Championships |
| 27. | 16 | 11 | Miguel Flores Ruiz | 17:33.1PR | CT | Hamden | Oct 10
| Hamden VS Career, Guilford, & Sheehan |
| 28. | | 12 | Derek Bratz | 17:33.2PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 29. | | 12 | Henry Murphy | 17:34.5 | CT | Lyman Hall | Oct 18
| SCC Cross Country Championships |
| 30. | | 12 | Jacob Merenda | 17:40.3 | CT | Daniel Hand | Oct 18
| SCC Cross Country Championships |
| 31. | | 12 | Cooper Woods | 17:42.6PR | CT | Guilford | Sep 23
| 16th Ocean State XC Invitational |
| 32. | | 12 | Jack Barney | 17:43.0PR | CT | Notre Dame-West Haven | Sep 19
| ND/SHA Duals |
| 33. | | 12 | Jack Lengyel | 17:52.3PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 34. | | 10 | Aaron Kowalonek | 17:52.6PR | CT | Guilford | Oct 18
| SCC Cross Country Championships |
| 35. | 18 | 12 | Daniel Manning | 17:53.7PR | CT | Amity | Oct 18
| SCC Cross Country Championships |
| 36. | | 10 | Ryan Glen | 17:53.8PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 37. | 18 | 12 | Ty Boucino | 17:56.0 | CT | Daniel Hand | Sep 19
| ND/SHA Duals |
| 38. | 17 | 12 | Charlie Santa | 17:56.6PR | CT | Fairfield Prep | Sep 23
| 16th Ocean State XC Invitational |
| | | 12 | Bryan Medina | 17:56.6PR | CT | Sheehan | Oct 18
| SCC Cross Country Championships |
| 40. | | 11 | Ethan Wienkamp | 17:56.9PR | CT | Guilford | Oct 10
| Hamden VS Career, Guilford, & Sheehan |
| 41. | 15 | 10 | Joseph Meade | 17:58.1PR | CT | Foran | Oct 18
| SCC Cross Country Championships |
| 42. | | 11 | Noah Hauswirth | 17:58.8PR | CT | Branford | Oct 18
| SCC Cross Country Championships |
| 43. | 17 | 12 | Mekkhi Adkins | 18:04.1PR | CT | Hillhouse | Oct 18
| SCC Cross Country Championships |
| 44. | | 10 | Matt Randall | 18:04.9PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 45. | | 12 | Eli Green-Perez | 18:06.3PR | CT | Guilford | Oct 18
| SCC Cross Country Championships |
| 46. | | 9 | David Zhang | 18:09.4PR | CT | Guilford | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 47. | 16 | 11 | Zayed Elahee | 18:10.3PR | CT | Hamden | Oct 18
| SCC Cross Country Championships |
| 48. | | 11 | Bank Tighe | 18:13.6PR | CT | West Haven | Oct 18
| SCC Cross Country Championships |
| 49. | 12 | 12 | James Galaburri | 18:18.8PR | CT | Foran | Oct 18
| SCC Cross Country Championships |
| 50. | 15 | 10 | Liam Stutz | 18:18.9PR | CT | Xavier (CT) | Sep 12
| Amity Duals 2023 |
| 51. | | 11 | Matthew DeNardis | 18:20.0PR | CT | North Haven | Oct 18
| SCC Cross Country Championships |
| 52. | | 12 | Alex Milano | 18:20.1PR | CT | Guilford | Sep 9
| 34th Wilton XC Invitational |
| 53. | | 11 | Enzo Taverna | 18:22.1PR | CT | Guilford | Sep 23
| 16th Ocean State XC Invitational |
| 54. | | 12 | Ben Jacoby | 18:23.3PR | CT | Daniel Hand | Oct 18
| SCC Cross Country Championships |
| 55. | | 9 | Lewis Thoreen | 18:24.0PR | CT | Guilford | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 56. | | 12 | Connor Pensa | 18:25.2 | CT | Guilford | Oct 18
| SCC Cross Country Championships |
| 57. | | 11 | Alexander Baneat | 18:27.5PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 58. | 15 | 10 | Zayd Vohra | 18:27.6PR | CT | Hamden | Oct 10
| Hamden VS Career, Guilford, & Sheehan |
| 59. | 16 | 10 | Liam Van Tonder | 18:28.0PR | CT | Amity | Oct 18
| SCC Cross Country Championships |
| 60. | | 11 | Jack Rickleman | 18:28.8PR | CT | Daniel Hand | Oct 18
| SCC Cross Country Championships |
| 61. | | 12 | Matt Pagan | 18:31.0PR | CT | West Haven | Oct 18
| SCC Cross Country Championships |
| 62. | 15 | 10 | Marco Blakeslee | 18:35.0PR | CT | Notre Dame-West Haven | Sep 19
| ND/SHA Duals |
| 63. | 16 | 11 | Daniel Tristine | 18:35.9PR | CT | Fairfield Prep | Oct 18
| SCC Cross Country Championships |
| 64. | | 11 | Austin Brothers | 18:36.3PR | CT | West Haven | Oct 18
| SCC Cross Country Championships |
| 65. | | 9 | Luca Esposito-Langl... | 18:40.7PR | CT | Guilford | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 66. | | 10 | Marco Blackslee | 18:41.2PR | CT | Notre Dame-West Haven | Oct 18
| SCC Cross Country Championships |
| 67. | | 12 | Paul Pavliouk | 18:42.1PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 68. | | 12 | Hunter Feitel | 18:42.4PR | CT | Xavier (CT) | Oct 18
| SCC Cross Country Championships |
| | 16 | 11 | Brent Wang | 18:42.4PR | | 05-Unattached | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 70. | 16 | 11 | Alexander Cuzio | 18:43.4 | CT | Amity | Oct 18
| SCC Cross Country Championships |
| 71. | | 11 | James Henderson | 18:44.4PR | CT | Xavier (CT) | Sep 18
| Wilbur Cross Duals 2023 |
| 72. | | 12 | Brian Krzanowski | 18:44.6 | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 73. | 17 | 12 | Charles Coughlin | 18:44.9PR | CT | North Haven | Oct 18
| SCC Cross Country Championships |
| 74. | | 12 | Ryan Zimmermann | 18:46.6 | CT | Xavier (CT) | Oct 18
| SCC Cross Country Championships |
| | | 10 | Alberto Torres | 18:46.6PR | CT | Notre Dame-West Haven | Oct 18
| SCC Cross Country Championships |
| 76. | | 12 | Ronan Liu | 18:47.3PR | CT | Sheehan | Sep 18
| Wilbur Cross Duals 2023 |
| 77. | 16 | 10 | Zachary Chasen | 18:47.5PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 78. | 15 | 10 | David Lickteig | 18:49.0PR | CT | Jonathan Law | Oct 18
| SCC Cross Country Championships |
| 79. | | 9 | Tyler Mezrich | 18:51.5PR | CT | Guilford | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 80. | | 9 | Peter Torello | 18:51.9PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 81. | | 10 | John Simpson | 18:52.0PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| | | 10 | Lucas Cohen | 18:52.0PR | CT | Amity | Oct 28
| CIAC Division L Boys Championship |
| 83. | | 9 | John McGuire | 18:57.0PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 84. | | 9 | Barrett Mullahy | 18:58.0PR | CT | Fairfield Prep | Oct 10
| Cheshire, Foran, East Haven, Prep@Lauralton H... |
| 85. | | 11 | Sam Kim | 19:00.4PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 86. | | 10 | Gabriel Grassi | 19:02.0PR | CT | Guilford | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 87. | | 12 | Devin Welch | 19:02.2 | CT | Sheehan | Oct 10
| Hamden VS Career, Guilford, & Sheehan |
| 88. | | 12 | Joseph Vostinak | 19:02.5PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 89. | 16 | 11 | William Kane | 19:03.0PR | CT | Fairfield Prep | Oct 10
| Cheshire, Foran, East Haven, Prep@Lauralton H... |
| | | 12 | Christofer Ramirez | 19:03.0 | CT | Wilbur Cross | Oct 28
| CIAC Division LL Boys Championship |
| 91. | 17 | 11 | Timothy Conklin | 19:03.3PR | CT | Lyman Hall | Oct 18
| SCC Cross Country Championships |
| 92. | | 12 | Mackinley Cho | 19:03.4PR | CT | Guilford | Sep 9
| 34th Wilton XC Invitational |
| 93. | | 10 | Hanan Talipan Pined... | 19:03.5PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 94. | | 12 | Henry Peeler | 19:09.6 | CT | Xavier (CT) | Sep 12
| Amity Duals 2023 |
| | | 9 | Jordan Espinosa | 19:09.6PR | CT | Guilford | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 96. | | 12 | Christopher Bonavit... | 19:13.6 | CT | Daniel Hand | Oct 18
| SCC Cross Country Championships |
| 97. | | 11 | Oliver Guzy | 19:14.0PR | CT | Xavier (CT) | Oct 18
| SCC Cross Country Championships |
| 98. | | 11 | Justin Li | 19:17.9PR | CT | Daniel Hand | Oct 18
| SCC Cross Country Championships |
| 99. | 15 | 10 | Adrian Koola | 19:18.0PR | CT | Amity | Oct 28
| CIAC Division L Boys Championship |
| 100. | | 11 | Owen Telesmanick | 19:20.1PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |