| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 16 | 11 | Soheib Dissa | 15:31.3PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 2. | 17 | 11 | Jack Ouellette | 15:32.3PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 3. | 16 | 11 | Owen Martin | 15:42.9PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 4. | 18 | 12 | Collin Walsh | 15:59.0 | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 5. | 16 | 10 | Luke Cushing | 16:03.0PR | CT | Amity | Nov 6
| CIAC State Open Boys Championship |
| 6. | | 12 | Cameron Nephew | 16:07.1PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 7. | 17 | 11 | Ryan Boulanger | 16:08.8PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 8. | 18 | 12 | Luke Davis | 16:12.8 | CT | Simsbury | Sep 19
| Conard, Simsbury @ Avon |
| 9. | | 12 | John Larkin | 16:16.7PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| | 17 | 12 | Daniel Coyne | 16:16.7PR | CT | Simsbury | Nov 11
| New England Interscholastic XC Championships |
| 11. | 17 | 12 | Benjamin Daniels | 16:20.0 | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 12. | 18 | 12 | Ben Schipul | 16:30.0PR | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 13. | 18 | 12 | Evan Piccioli | 16:34.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 14. | 2 | 12 | Alex Cohen | 16:35.0 | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| 15. | | 11 | Ian Schmeelk | 16:37.0PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 16. | 16 | 11 | Grant Bigger | 16:41.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 17. | 16 | 11 | Owen Jones | 16:52.0PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 18. | | 12 | Caleb Cerra | 16:53.9 | CT | New Milford | Nov 11
| New England Interscholastic XC Championships |
| 19. | | 11 | Charlie Lechowicz | 16:54.1PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 20. | 17 | 12 | Daniel D'Souza | 16:55.6PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 21. | | 11 | Owen Gluck | 17:02.0PR | CT | Darien | Oct 18
| FCIAC Cross Country Championships |
| 22. | 16 | 10 | Braden Barber | 17:03.0PR | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| 23. | | 12 | Jack Larkin | 17:07.4PR | CT | Xavier (CT) | Sep 23
| Bowdoin Park XC Classic |
| 24. | | 12 | Patrick Wininger | 17:08.0PR | CT | Bristol Central | Oct 3
| Middletown Vs Bristol Central/Maloney |
| 25. | 16 | 11 | Jason Costa | 17:10.9PR | CT | Naugatuck | Sep 30
| 64th Nonnewaug XC Invitational |
| 26. | | 12 | Sawyer Bloom | 17:11.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 27. | | 10 | Andrew Hawk | 17:13.0PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 28. | | 12 | Tyler Caron | 17:13.2 | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 29. | 17 | 12 | Noah Masotta | 17:13.6PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 30. | 17 | 12 | Neev Kanwar | 17:14.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 31. | 17 | 12 | Jacob Kozar | 17:14.2PR | CT | New Canaan | Sep 19
| Wilton, Norwalk, Ludlowe at New Canaan |
| 32. | 16 | 11 | John Disturco | 17:16.3PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 33. | 17 | 12 | Sean Morley | 17:17.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 34. | 15 | 10 | Andrew Sharron | 17:18.0PR | CT | Darien | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 35. | | 11 | Joseph Lechowicz | 17:19.0PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 36. | 17 | 11 | Spencer Paine | 17:21.0 | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| 37. | 18 | 12 | Brenner Patrick | 17:24.8PR | CT | Simsbury | Oct 14
| 62nd Catholic Memorial Invitational |
| 38. | | 10 | Landon Rubano | 17:25.8PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 39. | | 11 | James Boyd | 17:26.4PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 40. | 17 | 12 | Jacob Fagan | 17:29.3PR | CT | Xavier (CT) | Oct 18
| SCC Cross Country Championships |
| 41. | | 10 | Caleb Davis | 17:29.5PR | CT | Simsbury | Sep 19
| Conard, Simsbury @ Avon |
| 42. | 16 | 10 | Ryan Jordan | 17:32.4PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 43. | | 12 | Derek Bratz | 17:33.2PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 44. | | 12 | William Forrest | 17:44.0PR | CT | Fairfield Ludlowe | Oct 18
| FCIAC Cross Country Championships |
| 45. | 3 | 11 | Faizal Zakir Hussai... | 17:45.0PR | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| 46. | | 11 | Aiden Padros | 17:49.0PR | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 47. | | 12 | William Hanington | 17:50.0 | CT | Fairfield Ludlowe | Oct 2
| McMahon, Warde, Trumbull at Ludlowe |
| 48. | | 12 | Andrew Li | 17:50.8PR | CT | Darien | Oct 3
| Darien, Bridgeport, Norwalk at Staples |
| 49. | | 12 | Jack Lengyel | 17:52.3PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 50. | 17 | 12 | Zachary McCasland | 17:53.4PR | CT | Naugatuck | Sep 30
| 64th Nonnewaug XC Invitational |
| 51. | 18 | 12 | Daniel Manning | 17:53.7PR | CT | Amity | Oct 18
| SCC Cross Country Championships |
| 52. | | 10 | Ryan Glen | 17:53.8PR | CT | Xavier (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 53. | | 12 | Pasquale Hoffman | 17:59.0PR | CT | Darien | Oct 18
| FCIAC Cross Country Championships |
| 54. | | 11 | Lucas Weaver | 18:00.0PR | CT | Fairfield Ludlowe | Oct 18
| FCIAC Cross Country Championships |
| 55. | 17 | 12 | Andrew Reed | 18:02.0PR | CT | New Canaan | Sep 27
| Staples, Trumbull, Westhill at New Canaan |
| 56. | | 12 | Aidan Walsh | 18:03.5PR | CT | South Windsor | Oct 13
| 11th Harry Geraghty XC Invite |
| 57. | 17 | 12 | Mekkhi Adkins | 18:04.1PR | CT | Hillhouse | Oct 18
| SCC Cross Country Championships |
| 58. | | 10 | Matt Randall | 18:04.9PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 59. | | 11 | William Erickson | 18:05.0PR | CT | Fairfield Ludlowe | Oct 2
| McMahon, Warde, Trumbull at Ludlowe |
| | 18 | 12 | Griffin Depalma | 18:05.0PR | CT | Maloney | Oct 3
| Middletown Vs Bristol Central/Maloney |
| 61. | | 10 | Jacob Crevani | 18:08.0PR | CT | Fairfield Ludlowe | Oct 18
| FCIAC Cross Country Championships |
| 62. | 16 | 11 | Kaamil Badami | 18:09.0PR | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| 63. | 18 | 12 | Jaydon Schuler | 18:10.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 64. | 16 | 11 | Zephyr Yeager | 18:12.0PR | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| | | 12 | Thomas Aponte | 18:12.0 | CT | Darien | Oct 18
| FCIAC Cross Country Championships |
| 66. | | 12 | Aven Mallie | 18:15.0PR | CT | Darien | Oct 18
| FCIAC Cross Country Championships |
| | | 10 | Avner Wilson-Spiro | 18:15.0PR | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| 68. | 16 | 11 | Luke Dalton | 18:15.8PR | CT | Naugatuck | Sep 30
| 64th Nonnewaug XC Invitational |
| 69. | 15 | 10 | Liam Stutz | 18:18.9PR | CT | Xavier (CT) | Sep 12
| Amity Duals 2023 |
| 70. | 16 | 11 | Caleb Evans | 18:23.4PR | CT | Farmington | Oct 10
| Farmington @ Avon |
| 71. | 14 | 9 | Dyllan Asuncion | 18:25.8PR | CT | Stratford | Oct 18
| SWC Championship |
| 72. | | 11 | Alexander Baneat | 18:27.5PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 73. | | 10 | Ronan Conway | 18:28.0PR | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| | 16 | 10 | Liam Van Tonder | 18:28.0PR | CT | Amity | Oct 18
| SCC Cross Country Championships |
| 75. | | 12 | Colton Baker | 18:29.2 | CT | Fairfield Ludlowe | Sep 19
| Wilton, Norwalk, Ludlowe at New Canaan |
| 76. | | 12 | Liam Moriarty | 18:30.0PR | CT | Fairfield Ludlowe | Oct 2
| McMahon, Warde, Trumbull at Ludlowe |
| | | 10 | William Oksanen | 18:30.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 78. | | 12 | Andrew Arena | 18:30.4PR | CT | Newtown | Oct 18
| SWC Championship |
| 79. | 17 | 12 | Finlay Kaeyer | 18:32.0PR | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| 80. | | 10 | Roman Gagliardi | 18:33.0PR | CT | Darien | Oct 18
| FCIAC Cross Country Championships |
| 81. | 16 | 11 | Eddie Dalton | 18:33.1PR | CT | Naugatuck | Sep 15
| Blue Dragon Invitational |
| 82. | 17 | 12 | Joseph Cervone | 18:35.0PR | CT | Naugatuck | Sep 30
| 64th Nonnewaug XC Invitational |
| 83. | 16 | 11 | Will Merritt | 18:36.5PR | CT | New Canaan | Sep 27
| Staples, Trumbull, Westhill at New Canaan |
| 84. | 16 | 10 | Santiago Rodriguez | 18:39.5PR | CT | Newington | Oct 17
| CCC XC Championships |
| 85. | | 12 | Ryan Pilon | 18:42.0PR | CT | Simsbury | Sep 27
| Farmington vs NWC and Simsbury at Winding Tra... |
| 86. | | 12 | Paul Pavliouk | 18:42.1PR | CT | Shelton | Oct 18
| SCC Cross Country Championships |
| 87. | | 12 | Hunter Feitel | 18:42.4PR | CT | Xavier (CT) | Oct 18
| SCC Cross Country Championships |
| 88. | 16 | 11 | Alexander Cuzio | 18:43.4 | CT | Amity | Oct 18
| SCC Cross Country Championships |
| 89. | | 12 | John Henry Kresser | 18:44.0PR | CT | Fairfield Ludlowe | Oct 18
| FCIAC Cross Country Championships |
| 90. | | 11 | James Henderson | 18:44.4PR | CT | Xavier (CT) | Sep 18
| Wilbur Cross Duals 2023 |
| 91. | | 12 | Brian Krzanowski | 18:44.6 | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| 92. | 3 | 12 | Colin Smith | 18:46.0PR | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| 93. | | 12 | Almy Moffitt | 18:46.1PR | CT | South Windsor | Oct 13
| 11th Harry Geraghty XC Invite |
| 94. | | 12 | Ryan Zimmermann | 18:46.6 | CT | Xavier (CT) | Oct 18
| SCC Cross Country Championships |
| 95. | | 11 | Brian Sallese | 18:47.2PR | CT | Wilton | Oct 11
| McMahon, Stamford, Staples at Wilton |
| 96. | 16 | 10 | Zachary Chasen | 18:47.5PR | CT | Cheshire | Oct 18
| SCC Cross Country Championships |
| | | 9 | Jacob Clyne | 18:47.5PR | CT | Middletown (CT) | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 98. | 16 | 11 | Daniel Gomez | 18:48.8PR | CT | Simsbury | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 99. | | 11 | John Frieders | 18:49.0PR | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| | | 11 | Shawn Cardamone | 18:49.0PR | CT | Newtown | Oct 28
| CIAC Division L Boys Championship |
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