| 1441 | 255 | | Reid | Hester | Northwestern Regional | 7 | 14:47.32 | 8:42 | 9:46 |
| 2113 | 256 | 168 | Anthony | Desantis | Swift | 6 | 14:48.71 | 8:43 | 9:46 |
| 1842 | 257 | | Henry | Pierpont | Shelton | 7 | 14:49.42 | 8:44 | 9:44 |
| 986 | 258 | | Jackson | Pugliese | Joseph A. Depaolo | 8 | 14:50.62 | 8:44 | 9:49 |
| 376 | 259 | 169 | John | Schilsmann | E. C. Adams | 7 | 14:50.69 | 8:44 | 9:36 |
| 1142 | 260 | 170 | Aiden | Ericksen | Litchfield | 8 | 14:50.83 | 8:45 | 9:22 |
| 453 | 261 | 171 | Adam | Speakman | Eli Terry Jr. | 8 | 14:51.86 | 8:45 | 9:53 |
| 1302 | 262 | | Ciaran | Flanagan | Memorial | 8 | 14:52.44 | 8:45 | 9:39 |
| 1043 | 263 | | Matt | Zeman | King Philip | 8 | 14:53.02 | 8:46 | 9:51 |
| 441 | 264 | 172 | Oliver | Garceau | Eli Terry Jr. | 7 | 14:53.07 | 8:46 | 9:44 |
| 934 | 265 | | Ryan | Hemingway | John F. Kennedy (Plantsville) | 8 | 14:53.68 | 8:46 | 9:37 |
| 719 | 266 | | Stefan | Feher | Hillcrest | 8 | 14:55.23 | 8:47 | 9:41 |
| 2381 | 267 | 173 | Alex | Krajeski | Woodbury | 6 | 14:57.40 | 8:48 | 9:52 |
| 1428 | 268 | | Hudson | Lusk | North Haven | 6 | 14:58.31 | 8:49 | 9:50 |
| 261 | 269 | | James | Korowotny | City Hill | 8 | 14:58.51 | 8:49 | 10:00 |
| 989 | 270 | | Joe | Sabino | Joseph A. Depaolo | 8 | 14:59.88 | 8:50 | 9:56 |
| 450 | 271 | 174 | Nick | Perugini | Eli Terry Jr. | 6 | 15:03.81 | 8:52 | 10:02 |
| 1810 | 272 | 175 | Sawyer | Bloom | Sedgwick | 8 | 15:03.92 | 8:52 | 9:48 |
| 38 | 273 | | Daniel | Pereira | Assumption Catholic | 5 | 15:05.83 | 8:53 | 9:40 |
| 2125 | 274 | | Connor | Segers | Swift | 6 | 15:07.44 | 8:54 | 9:48 |
| 884 | 275 | | Nicholas | Renda | James H. Moran | 6 | 15:07.54 | 8:54 | 9:56 |
| 342 | 276 | | Mason | Izquierelo | Derby | 7 | 15:08.09 | 8:55 | 10:04 |
| 1486 | 277 | 176 | Gavin | Unwin | Our Lady Of Mount Carmel | 7 | 15:10.19 | 8:56 | 10:04 |
| 2011 | 278 | | Teddy | Doyle | St. Timothy | 8 | 15:10.65 | 8:56 | 10:04 |
| 348 | 279 | | Roman | Sowell | Derby | 6 | 15:10.67 | 8:56 | 10:09 |
| 207 | 280 | 177 | Jonathan | M | Catholic Academy Waterbury | 7 | 15:15.08 | 8:59 | 10:03 |
| 571 | 281 | 178 | Nicholas | Pavlidis | Gilbert | 8 | 15:21.23 | 9:02 | 10:06 |
| 197 | 282 | | Maddox | Rodriguez | Catherine Mcgee | 7 | 15:21.34 | 9:02 | 9:59 |
| 1303 | 283 | | Grayson | Mengold | Memorial | 6 | 15:21.62 | 9:03 | 10:11 |
| 190 | 284 | | Nico | Fiducia | Catherine Mcgee | 6 | 15:21.68 | 9:03 | 9:55 |
| 451 | 285 | 179 | Colby | Pronovost | Eli Terry Jr. | 7 | 15:24.50 | 9:04 | 9:56 |
| 1815 | 286 | 180 | Henry | Plocharczyk | Sedgwick | 7 | 15:26.74 | 9:06 | 10:14 |
| 489 | 287 | 181 | Fereol | Faure | Foote | 7 | 15:28.03 | 9:06 | 10:20 |
| 2110 | 288 | | Sebastian | Creter | Swift | 7 | 15:30.64 | 9:08 | 10:22 |
| 1234 | 289 | | Henry | Kunkel | Madison | 6 | 15:30.66 | 9:08 | 10:07 |
| 495 | 290 | 182 | Deyi | Meng | Foote | 6 | 15:32.44 | 9:09 | 10:13 |
| 724 | 291 | | Jacob | Levin | Hillcrest | 7 | 15:33.64 | 9:10 | 10:03 |
| 438 | 292 | 183 | Marcus | Dunn | Eli Terry Jr. | 6 | 15:35.22 | 9:11 | 10:09 |
| 204 | 293 | 184 | Stephen | Dehoney | Catholic Academy Waterbury | 6 | 15:36.00 | 9:11 | 10:12 |
| 570 | 294 | 185 | Xzayvier | Kelley | Gilbert | 7 | 15:37.27 | 9:12 | 10:19 |
| 1480 | 295 | 186 | Tavis | Currier | Our Lady Of Mount Carmel | 5 | 15:40.62 | 9:14 | 10:10 |
| 439 | 296 | | John | Fitzherbert | Eli Terry Jr. | 8 | 15:40.87 | 9:14 | 10:41 |
| 2126 | 297 | | William | Simonsen | Swift | 6 | 15:42.30 | 9:15 | 10:17 |
| 1808 | 298 | 187 | Jay | Arleth | Sedgwick | 6 | 15:42.72 | 9:15 | 10:11 |
| 2010 | 299 | | Blaise | Doyle | St. Timothy | 6 | 15:44.90 | 9:16 | 10:14 |
| 2115 | 300 | | Nathan | Fenn | Swift | 7 | 15:45.12 | 9:16 | 10:23 |
| 927 | 301 | | Shane | Barry | John F. Kennedy (Plantsville) | 7 | 15:45.60 | 9:17 | 10:14 |
| 940 | 302 | | Gavin | Pettit | John F. Kennedy (Plantsville) | 6 | 15:45.84 | 9:17 | 10:14 |
| 2263 | 303 | 188 | Zachary | Abramowitz | Westport United Track Club | | 15:47.84 | 9:18 | 10:28 |
| 269 | 304 | | Jordan | Stango | City Hill | 7 | 15:48.50 | 9:18 | 10:23 |
| 928 | 305 | | Jacob | Lowe | John F. Kennedy (Plantsville) | 6 | 15:53.85 | 9:22 | 10:22 |
| 298 | 306 | | Thomas | Matropetro | Dag Hammarskjold | 6 | 15:53.90 | 9:22 | 10:36 |
| 572 | 307 | 189 | Anhkhoa | Pham | Gilbert | 7 | 15:58.86 | 9:25 | 10:27 |
| 259 | 308 | | Sean | Green | City Hill | 7 | 16:02.88 | 9:27 | 10:32 |
| 929 | 309 | | Carson | Cook | John F. Kennedy (Plantsville) | 6 | 16:04.51 | 9:28 | 10:26 |
| 258 | 310 | | Tim | Gairing | City Hill | 8 | 16:04.84 | 9:28 | 10:31 |
| 1235 | 311 | | Owen | Leclerc | Madison | 8 | 16:06.12 | 9:29 | 10:19 |
| 2124 | 312 | | Sashore | Savariau | Swift | 6 | 16:07.09 | 9:29 | 10:47 |
| 445 | 313 | | Kristian | Kwoczala | Eli Terry Jr. | 8 | 16:07.50 | 9:30 | 10:13 |
| 1424 | 314 | | Grant | Grotzke | North Haven | 7 | 16:09.08 | 9:31 | 10:27 |
| 1141 | 315 | | Mike | Delayo | Litchfield | 7 | 16:09.28 | 9:31 | 10:37 |
| 932 | 316 | | Jayden | Campbell | John F. Kennedy (Plantsville) | 6 | 16:14.24 | 9:34 | 10:30 |
| 347 | 317 | | Joseph | Izquierelo | Derby | 7 | 16:14.66 | 9:34 | 10:44 |
| 933 | 318 | | Owen | Graven | John F. Kennedy (Plantsville) | 6 | 16:15.16 | 9:34 | 10:43 |
| 2116 | 319 | | Jacob | Mendello | Swift | 6 | 16:16.19 | 9:35 | 10:47 |
| 183 | 320 | | Brayden | Bak | Catherine Mcgee | 6 | 16:26.62 | 9:41 | 10:53 |
| 435 | 321 | | Noah | Botto | Eli Terry Jr. | 8 | 16:28.45 | 9:42 | 10:56 |
| 181 | 322 | | Jaeden | Aichele | Catherine Mcgee | 6 | 16:36.13 | 9:46 | 10:52 |
| 2380 | 323 | 190 | Layne | Klingman | Woodbury | 8 | 16:36.59 | 9:47 | 11:16 |
| 566 | 324 | 191 | Alexander | Bunel | Gilbert | 8 | 16:37.06 | 9:47 | 11:00 |
| 2374 | 325 | | Dylan | Duda | Woodbury | 8 | 16:38.37 | 9:48 | 11:19 |
| 1954 | 326 | 192 | Nicholas | Feola | St. Bridget | 6 | 16:46.44 | 9:53 | 10:58 |
| 936 | 327 | | Jonathan | Pillsbury | John F. Kennedy (Plantsville) | 8 | 16:49.64 | 9:54 | 10:55 |
| 443 | 328 | | Layne | Holt | Eli Terry Jr. | 8 | 16:52.03 | 9:56 | 10:55 |
| 373 | 329 | 193 | Ben | Libby | E. C. Adams | 7 | 16:52.60 | 9:56 | 11:15 |
| 873 | 330 | | Fernando | Gonzalez | James H. Moran | 8 | 17:00.18 | 10:01 | 10:49 |
| 565 | 331 | | Andrew | Beach | Gilbert | 7 | 17:02.56 | 10:02 | 11:12 |
| 377 | 332 | 194 | Wiley | VanSteenberge | E. C. Adams | 7 | 17:24.41 | 10:15 | 10:47 |
| 447 | 333 | | Nathan | Lavallee | Eli Terry Jr. | 6 | 17:34.37 | 10:21 | 11:14 |
| 208 | 334 | 195 | James | Rinaldi | Catholic Academy Waterbury | 8 | 17:40.95 | 10:25 | 11:19 |
| 683 | 335 | 196 | Aiden | Diaz | Hals Academy | 8 | 17:43.48 | 10:26 | 11:43 |
| 2377 | 336 | | Brycen | Gagne | Woodbury | 6 | 17:49.34 | 10:30 | 11:59 |
| 2376 | 337 | | Tommy | Faull | Woodbury | 8 | 17:49.86 | 10:30 | 11:41 |
| 488 | 338 | 197 | Jake | Fasano | Foote | 6 | 17:51.13 | 10:31 | 12:14 |
| 1857 | 339 | | Jake | Gervasio | Shepaug Valley | 6 | 17:51.53 | 10:31 | 12:06 |
| 485 | 340 | 198 | Matias | Candelo-Diaz | Foote | 7 | 18:28.10 | 10:52 | 12:23 |
| 2385 | 341 | | Joseph | Witte | Woodbury | 8 | 18:43.27 | 11:01 | 12:05 |
| 1380 | 342 | | Jake | Green | New Fairfield | 7 | 18:52.71 | 11:07 | 12:37 |
| 866 | 343 | | Julien | Mange | James H. Moran | 7 | 18:53.37 | 11:07 | 12:29 |
| 37 | 344 | | Donovan | Nascimento | Assumption Catholic | 6 | 18:55.22 | 11:08 | 12:30 |
| 1956 | 345 | 199 | Saleem | Khan | St. Bridget | 8 | 19:00.47 | 11:11 | 12:40 |
| 1814 | 346 | 200 | Joshua | Peak | Sedgwick | 7 | 19:18.80 | 11:22 | 12:29 |
| 1963 | 347 | 201 | Grady | Vogt | St. Bridget | 8 | 19:36.01 | 11:32 | 12:44 |
| 179 | 348 | | Alexander | Ahlquist | Catherine Mcgee | 6 | 19:52.81 | 11:42 | 12:47 |
| 1961 | 349 | 202 | Stephen | Tine | St. Bridget | 6 | 19:58.46 | 11:45 | 12:45 |
| 490 | 350 | | Aydin | Gasimov | Foote | 6 | 20:07.87 | 11:51 | 13:03 |
| 568 | 351 | | Arian | Gutic | Gilbert | 7 | 20:26.07 | 12:02 | 12:55 |
| 569 | 352 | | Lucas | Holda | Gilbert | 8 | 21:49.81 | 12:51 | 13:30 |
| 1962 | 353 | | Arjun | Vashist | St. Bridget | 5 | 22:00.64 | 12:57 | 14:32 |
| 1940 | 354 | | Derek | Harrison | St. Anthony | 7 | 22:56.21 | 13:30 | 15:24 |