| 1 | 17:49.49 | Lexington Catholic | 2017 | |
| 2 | 18:00.79 | Lexington Catholic | 2017 | |
| 3 | 18:06.84 | Lafayette | 2017 | |
| 4 | 18:44.71 | Lexington Catholic | 2017 | |
| 5 | 18:55.79 | Ryle | 2016 | |
| 6 | 19:15.58 | Williamsburg | 2019 | |
| 7 | 19:18.98 | Williamsburg | 2019 | |
| 8 | 19:20.00 | Tates Creek | 2017 | |
| 9 | 19:26.68 | Woodford County | 2019 | |
| 10 | 19:31.81 | Woodford County | 2019 | |
| 11 | 19:39.36 | Ryle | 2018 | |
| 12 | 19:49.15 | Tates Creek | 2019 | |
| 13 | 19:49.27 | Henry Clay | 2016 | |
| 14 | 19:57.19 | Paul Dunbar | 2018 | |
| 15 | 19:58.91 | Lexington Christian | 2019 | |
| 16 | 20:02.14 | Lloyd Memorial | 2014 | |
| 17 | 20:03.05 | Tates Creek | 2018 | |
| 18 | 20:05.22 | Ryle | 2016 | |
| 19 | 20:05.83 | Pulaski County | 2019 | |
| 20 | 20:10.48 | Tates Creek | 2018 | |
| 21 | 20:13.78 | Ryle | 2018 | |
| 22 | 20:16.14 | Ryle | 2018 | |
| 23 | 20:19.71 | Woodford County | 2014 | |
| 24 | 20:30.13 | Woodford County | 2017 | |
| 25 | 20:30.38 | Ryle | 2018 | |
| 26 | 20:30.52 | Scott County | 2016 | |
| 27 | 20:30.95 | Conner | 2018 | |
| 28 | 20:33.70 | Grayson County | 2019 | |
| 29 | 20:34.76 | Tates Creek | 2014 | |
| 30 | 20:37.37 | Lexington Catholic | 2015 | |
| 31 | 20:38.36 | Pulaski County | 2020 | |
| 32 | 20:38.86 | Ryle | 2017 | |
| 33 | 20:38.98 | Corbin | 2018 | |
| 34 | 20:39.76 | Ryle | 2016 | |
| 35 | 20:40.69 | Tates Creek | 2014 | |
| 36 | 20:42.09 | Henry Clay | 2016 | |
| 37 | 20:43.84 | Tates Creek | 2018 | |
| 38 | 20:48.59 | Lafayette | 2015 | |
| 39 | 20:48.82 | Tates Creek | 2014 | |
| 40 | 20:50.35 | North Hardin | 2016 | |
| 41 | 20:51.09 | Ryle | 2017 | |
| 42 | 20:52.04 | Ryle | 2015 | |
| 43 | 20:52.73 | Henry Clay | 2015 | |
| 44 | 20:53.43 | Lexington Catholic | 2018 | |
| 45 | 20:55.31 | Woodford County | 2017 | |
| 46 | 20:56.52 | Ryle | 2017 | |
| 47 | 20:56.70 | Pulaski County | 2017 | |
| 48 | 20:57.97 | Western Hills | 2021 | |
| 49 | 20:59.16 | Scott County | 2019 | |
| 50 | 21:00.42 | Conner | 2019 | |
| 51 | 21:00.64 | Ryle | 2018 | |
| 52 | 21:01.13 | South Laurel | 2016 | |
| 53 | 21:03.04 | Woodford County | 2017 | |
| 54 | 21:04.52 | Tates Creek | 2019 | |
| 55 | 21:06.80 | Tates Creek | 2015 | |
| 56 | 21:06.81 | Montgomery County | 2017 | |
| 57 | 21:08.36 | Henry Clay | 2015 | |
| 58 | 21:08.37 | Woodford County | 2015 | |
| 59 | 21:11.11 | Henry Clay | 2018 | |
| 60 | 21:11.19 | Wayne County | 2020 | |
| 61 | 21:12.53 | Woodford County | 2015 | |
| 62 | 21:12.71 | Lexington Catholic | 2014 | |
| 63 | 21:13.99 | Woodford County | 2016 | |
| 64 | 21:15.66 | Tates Creek | 2018 | |
| 65 | 21:15.95 | Pulaski County | 2021 | |
| 66 | 21:17.84 | Tates Creek | 2018 | |
| 67 | 21:18.33 | Tates Creek | 2019 | |
| 68 | 21:18.62 | North Laurel | 2019 | |
| 69 | 21:19.78 | Henry Clay | 2017 | |
| 70 | 21:20.07 | Montgomery County | 2021 | |
| 71 | 21:21.25 | Ryle | 2018 | |
| 72 | 21:21.55 | North Hardin | 2018 | |
| 73 | 21:23.02 | Tates Creek | 2015 | |
| 74 | 21:23.20 | West Jessamine | 2017 | |
| 75 | 21:23.23 | Ryle | 2017 | |
| 76 | 21:25.00 | Lexington Christian | 2017 | |
| 77 | 21:26.06 | West Jessamine | 2017 | |
| 78 | 21:26.58 | Henry Clay | 2016 | |
| 79 | 21:27.07 | Tates Creek | 2018 | |
| 80 | 21:28.11 | South Laurel | 2019 | |
| 81 | 21:28.58 | Spencer County | 2018 | |
| 82 | 21:29.02 | Tates Creek | 2015 | |
| 83 | 21:30.32 | Grayson County | 2018 | |
| 84 | 21:30.63 | Corbin | 2018 | |
| 85 | 21:30.98 | Henry Clay | 2016 | |
| 86 | 21:31.21 | John Hardin | 2019 | |
| 87 | 21:32.31 | Tates Creek | 2017 | |
| 88 | 21:35.16 | Corbin | 2018 | |
| 89 | 21:35.59 | Ryle | 2020 | |
| 90 | 21:36.78 | Henry Clay | 2018 | |
| 91 | 21:40.20 | Henry Clay | 2017 | |
| 92 | 21:40.43 | Lexington Catholic | 2014 | |
| 93 | 21:43.84 | Spencer County | 2019 | |
| 94 | 21:45.10 | Ryle | 2017 | |
| 95 | 21:45.43 | Montgomery County | 2017 | |
| 96 | 21:45.53 | Henry Clay | 2018 | |
| 97 | 21:46.42 | Webster County | 2019 | |
| 98 | 21:46.83 | Lexington Catholic | 2018 | |
| 99 | 21:47.99 | Henry Clay | 2016 | |
| 100 | 21:48.01 | Henry Clay | 2018 | |
| 101 | 21:49.23 | Villa Madonna | 2015 | |
| 102 | 21:49.76 | Lexington Catholic | 2019 | |
| 103 | 21:50.19 | Lexington Catholic | 2015 | |
| 104 | 21:50.95 | Lexington Catholic | 2016 | |
| 105 | 21:52.56 | Ryle | 2014 | |
| 106 | 21:52.65 | Webster County | 2019 | |
| 107 | 21:53.20 | Webster County | 2021 | |
| 108 | 21:53.54 | Woodford County | 2017 | |
| 109 | 21:53.66 | South Laurel | 2018 | |
| 110 | 21:54.14 | Henry Clay | 2017 | |
| 111 | 21:54.15 | Ryle | 2017 | |
| 112 | 21:55.36 | Villa Madonna | 2014 | |
| 113 | 21:55.42 | Scott County | 2017 | |
| 114 | 21:55.51 | Woodford County | 2015 | |
| 115 | 21:55.67 | Lexington Catholic | 2016 | |
| 116 | 21:56.14 | Corbin | 2014 | |
| 117 | 21:56.46 | Scott County | 2014 | |
| 118 | 21:56.47 | Pulaski County | 2019 | |
| 119 | 21:56.62 | Webster County | 2017 | |
| 120 | 21:56.85 | Henry Clay | 2017 | |
| 121 | 21:57.05 | Lloyd Memorial | 2017 | |
| 122 | 22:00.06 | Grayson County | 2018 | |
| 123 | 22:00.34 | Western Hills | 2017 | |
| 124 | 22:00.47 | Montgomery County | 2016 | |
| 125 | 22:01.67 | Pulaski County | 2021 | |
| 126 | 22:02.53 | Woodford County | 2017 | |
| 127 | 22:03.08 | Woodford County | 2018 | |
| 128 | 22:04.20 | Montgomery County | 2019 | |
| 129 | 22:05.43 | Tates Creek | 2015 | |
| 130 | 22:05.94 | Wayne County | 2019 | |
| 131 | 22:05.97 | Tates Creek | 2017 | |
| 132 | 22:06.02 | Tates Creek | 2017 | |
| 133 | 22:06.78 | Ryle | 2016 | |
| 134 | 22:07.15 | Lexington Catholic | 2017 | |
| 135 | 22:07.70 | Lexington Catholic | 2014 | |
| 136 | 22:08.34 | Lexington Christian | 2019 | |
| 137 | 22:10.35 | Tates Creek | 2020 | |
| 138 | 22:11.57 | Williamsburg | 2019 | |
| 139 | 22:12.08 | Ryle | 2018 | |
| 140 | 22:12.49 | Henry Clay | 2015 | |
| 141 | 22:18.05 | Grayson County | 2016 | |
| 142 | 22:18.36 | Lloyd Memorial | 2014 | |
| 143 | 22:18.80 | Ryle | 2018 | |
| 144 | 22:19.86 | Grayson County | 2017 | |
| 145 | 22:20.55 | Lafayette | 2015 | |
| 146 | 22:21.01 | Montgomery County | 2019 | |
| 147 | 22:21.03 | Tates Creek | 2018 | |
| 148 | 22:21.92 | Henry Clay | 2017 | |
| 149 | 22:22.02 | Lexington Catholic | 2016 | |
| 150 | 22:22.76 | Grayson County | 2018 | |
| 151 | 22:23.04 | Lafayette | 2021 | |
| 152 | 22:26.08 | Williamsburg | 2019 | |
| 153 | 22:27.93 | Corbin | 2017 | |
| 154 | 22:28.05 | Lexington Catholic | 2015 | |
| 155 | 22:28.38 | Paul Dunbar | 2019 | |
| 156 | 22:28.72 | North Hardin | 2020 | |
| 157 | 22:29.09 | Ryle | 2018 | |
| 158 | 22:29.23 | North Laurel | 2021 | |
| 159 | 22:30.00 | John Hardin | 2018 | |
| 160 | 22:32.25 | Henry Clay | 2014 | |
| 161 | 22:32.32 | Lexington Catholic | 2017 | |
| 162 | 22:33.44 | Anderson County | 2015 | |
| 163 | 22:34.47 | Lexington Catholic | 2017 | |
| 164 | 22:34.96 | Woodford County | 2017 | |
| 165 | 22:35.50 | Ryle | 2018 | |
| 166 | 22:35.59 | Henry Clay | 2017 | |
| 167 | 22:36.04 | Bell County | 2018 | |
| 168 | 22:38.12 | Tates Creek | 2018 | |
| 169 | 22:39.14 | Webster County | 2018 | |
| 170 | 22:39.62 | Ryle | 2018 | |
| 171 | 22:40.58 | Scott County | 2016 | |
| 172 | 22:40.93 | North Laurel | 2020 | |
| 173 | 22:41.15 | Woodford County | 2014 | |
| 174 | 22:42.34 | Webster County | 2018 | |
| 175 | 22:42.95 | Lexington Christian | 2020 | |
| 176 | 22:43.20 | Ryle | 2017 | |
| 177 | 22:44.31 | Williamsburg | 2019 | |
| 178 | 22:44.76 | Conner | 2019 | |
| 179 | 22:45.26 | Ryle | 2017 | |
| 180 | 22:47.18 | Ryle | 2018 | |
| 181 | 22:47.88 | Tates Creek | 2018 | |
| 182 | 22:48.39 | Lexington Christian | 2020 | |
| 183 | 22:48.46 | Sayre | 2019 | |
| 184 | 22:49.64 | Webster County | 2017 | |
| 185 | 22:50.81 | Ryle | 2016 | |
| 186 | 22:51.81 | Ryle | 2016 | |
| 187 | 22:52.15 | Tates Creek | 2015 | |
| 188 | 22:52.22 | Conner | 2020 | |
| 189 | 22:52.72 | Ryle | 2019 | |
| 190 | 22:52.90 | Lafayette | 2015 | |
| 191 | 22:55.14 | Ryle | 2017 | |
| 192 | 22:55.58 | Henry Clay | 2017 | |
| 193 | 22:56.36 | Western Hills | 2018 | |
| 194 | 22:56.75 | Henry Clay | 2017 | |
| 195 | 22:56.78 | Corbin | 2015 | |
| 196 | 22:57.43 | Tates Creek | 2015 | |
| 197 | 22:58.44 | West Jessamine | 2018 | |
| 198 | 22:58.54 | Lexington Catholic | 2016 | |
| 199 | 22:58.85 | John Hardin | 2021 | |
| 200 | 22:59.76 | Ryle | 2017 | |
| 201 | 23:00.51 | Henry Clay | 2014 | |
| 202 | 23:00.92 | Webster County | 2015 | |
| 203 | 23:01.73 | North Hardin | 2016 | |
| 204 | 23:06.08 | West Jessamine | 2016 | |
| 205 | 23:06.36 | Tates Creek | 2019 | |
| 206 | 23:06.53 | Webster County | 2018 | |
| 207 | 23:06.75 | Tates Creek | 2018 | |
| 208 | 23:09.52 | North Laurel | 2018 | |
| 209 | 23:09.80 | Lexington Catholic | 2016 | |
| 210 | 23:10.93 | Woodford County | 2015 | |
| 211 | 23:11.17 | Scott County | 2020 | |
| 212 | 23:12.46 | Henry Clay | 2016 | |
| 213 | 23:12.63 | Henry Clay | 2016 | |
| 214 | 23:13.02 | Villa Madonna | 2018 | |
| 215 | 23:13.97 | West Jessamine | 2015 | |
| 216 | 23:15.08 | Villa Madonna | 2014 | |
| 217 | 23:15.41 | Owen County | 2017 | |
| 218 | 23:17.78 | Ryle | 2016 | |
| 219 | 23:18.61 | Lexington Christian | 2019 | |
| 220 | 23:19.12 | Paul Dunbar | 2017 | |
| 221 | 23:20.07 | Lexington Catholic | 2014 | |
| 222 | 23:20.72 | West Jessamine | 2017 | |
| 223 | 23:21.97 | Tates Creek | 2015 | |
| 224 | 23:22.25 | Ryle | 2016 | |
| 225 | 23:22.79 | John Hardin | 2021 | |
| 226 | 23:25.63 | Ryle | 2018 | |
| 227 | 23:27.05 | North Laurel | 2019 | |
| 228 | 23:27.84 | Scott County | 2017 | |
| 229 | 23:31.74 | Conner | 2019 | |
| 230 | 23:32.26 | Lexington Catholic | 2014 | |
| 231 | 23:34.27 | Western Hills | 2017 | |
| 232 | 23:34.74 | Paul Dunbar | 2019 | |
| 233 | 23:37.36 | Ryle | 2016 | |
| 234 | 23:38.47 | Scott County | 2015 | |
| 235 | 23:38.61 | Henry Clay | 2017 | |
| 236 | 23:38.62 | Conner | 2019 | |
| 237 | 23:40.18 | Ryle | 2016 | |
| 238 | 23:40.48 | Lloyd Memorial | 2017 | |
| 239 | 23:40.52 | Lloyd Memorial | 2017 | |
| 240 | 23:40.69 | Woodford County | 2017 | |
| 241 | 23:41.11 | Woodford County | 2018 | |
| 242 | 23:44.32 | Trimble County | 2019 | |
| 243 | 23:45.22 | Grayson County | 2019 | |
| 244 | 23:46.56 | Henry Clay | 2017 | |
| 245 | 23:47.41 | Trimble County | 2021 | |
| 246 | 23:47.97 | Villa Madonna | 2016 | |
| 247 | 23:48.00 | Ryle | 2016 | |
| 248 | 23:48.49 | Conner | 2019 | |
| 249 | 23:48.95 | Lexington Catholic | 2016 | |
| 250 | 23:48.97 | Corbin | 2019 | |
| 251 | 23:49.40 | Montgomery County | 2017 | |
| 252 | 23:49.95 | Corbin | 2018 | |
| 253 | 23:51.22 | Lexington Catholic | 2014 | |
| 254 | 23:51.23 | North Laurel | 2020 | |
| 255 | 23:52.11 | Henry Clay | 2016 | |
| 256 | 23:52.65 | Grayson County | 2016 | |
| 257 | 23:52.84 | Webster County | 2019 | |
| 258 | 23:53.10 | Scott County | 2014 | |
| 259 | 23:53.63 | Henry Clay | 2017 | |
| 260 | 23:53.87 | Ryle | 2016 | |
| 261 | 23:53.94 | Owen County | 2016 | |
| 262 | 23:54.07 | South Laurel | 2019 | |
| 263 | 23:54.82 | Woodford County | 2018 | |
| 264 | 23:54.84 | Woodford County | 2016 | |
| 265 | 23:55.28 | West Jessamine | 2018 | |
| 266 | 23:55.35 | Henry Clay | 2019 | |
| 267 | 23:56.23 | Williamsburg | 2019 | |
| 268 | 23:56.69 | Lexington Catholic | 2016 | |
| 269 | 23:56.94 | Spencer County | 2019 | |
| 270 | 23:56.96 | Garrard County | 2018 | |
| 271 | 23:57.04 | Grayson County | 2019 | |
| 272 | 23:57.47 | Henry Clay | 2017 | |
| 273 | 23:57.48 | Webster County | 2015 | |
| 274 | 23:57.52 | Woodford County | 2018 | |
| 275 | 23:58.00 | Woodford County | 2015 | |
| 276 | 23:58.15 | Scott County | 2017 | |
| 277 | 23:58.67 | Ryle | 2018 | |
| 278 | 24:03.54 | Lloyd Memorial | 2018 | |
| 279 | 24:04.10 | Bryan Station | 2017 | |
| 280 | 24:04.13 | Ryle | 2016 | |
| 281 | 24:04.75 | Grayson County | 2018 | |
| 282 | 24:05.83 | West Jessamine | 2017 | |
| 283 | 24:06.22 | Scott County | 2019 | |
| 284 | 24:08.61 | Owen County | 2021 | |
| 285 | 24:08.98 | Owen County | 2016 | |
| 286 | 24:10.44 | North Hardin | 2016 | |
| 287 | 24:12.16 | Lloyd Memorial | 2015 | |
| 288 | 24:12.50 | Villa Madonna | 2018 | |
| 289 | 24:12.69 | Scott County | 2016 | |
| 290 | 24:13.98 | Lloyd Memorial | 2019 | |
| 291 | 24:16.46 | Trimble County | 2016 | |
| 292 | 24:16.50 | Western Hills | 2021 | |
| 293 | 24:16.96 | Lexington Catholic | 2016 | |
| 294 | 24:18.12 | Henry Clay | 2017 | |
| 295 | 24:18.31 | Lloyd Memorial | 2017 | |
| 296 | 24:19.99 | Webster County | 2015 | |
| 297 | 24:21.14 | Williamsburg | 2014 | |
| 298 | 24:22.55 | South Laurel | 2020 | |
| 299 | 24:24.67 | Lloyd Memorial | 2016 | |
| 300 | 24:26.15 | West Jessamine | 2016 | |
| 301 | 24:28.30 | Henry Clay | 2016 | |
| 302 | 24:28.31 | Bell County | 2019 | |
| 303 | 24:29.06 | Conner | 2018 | |
| 304 | 24:29.65 | Henry Clay | 2017 | |
| 305 | 24:30.19 | Ryle | 2019 | |
| 305 | 24:30.19 | Woodford County | 2017 | |
| 307 | 24:31.65 | Bryan Station | 2016 | |
| 308 | 24:35.14 | Woodford County | 2019 | |
| 309 | 24:36.11 | Woodford County | 2016 | |
| 310 | 24:36.80 | Bryan Station | 2017 | |
| 311 | 24:37.68 | Henry Clay | 2017 | |
| 312 | 24:38.55 | Scott County | 2016 | |
| 313 | 24:39.72 | Grayson County | 2018 | |
| 314 | 24:41.69 | Lloyd Memorial | 2017 | |
| 315 | 24:43.46 | Bryan Station | 2017 | |
| 316 | 24:44.69 | Henry Clay | 2019 | |
| 317 | 24:45.44 | Lexington Catholic | 2014 | |
| 318 | 24:45.96 | Sayre | 2018 | |
| 319 | 24:46.85 | West Jessamine | 2017 | |
| 320 | 24:47.57 | Owen County | 2017 | |
| 321 | 24:47.99 | Corbin | 2019 | |
| 322 | 24:48.00 | Lexington Catholic | 2017 | |
| 323 | 24:48.24 | Sayre | 2017 | |
| 324 | 24:48.28 | Henry Clay | 2017 | |
| 325 | 24:49.06 | Lexington Catholic | 2017 | |
| 326 | 24:52.18 | Henry Clay | 2014 | |
| 327 | 24:53.31 | Lexington Catholic | 2018 | |
| 328 | 24:55.41 | Lexington Christian | 2018 | |
| 329 | 24:55.88 | John Hardin | 2018 | |
| 330 | 24:56.81 | Ryle | 2017 | |
| 331 | 24:57.93 | Corbin | 2017 | |
| 332 | 25:02.90 | Woodford County | 2018 | |
| 333 | 25:02.94 | Grayson County | 2018 | |
| 334 | 25:03.35 | Owen County | 2016 | |
| 335 | 25:03.85 | North Hardin | 2018 | |
| 336 | 25:04.11 | Scott County | 2017 | |
| 337 | 25:04.61 | South Laurel | 2018 | |
| 338 | 25:05.00 | Ryle | 2017 | |
| 339 | 25:07.56 | Montgomery County | 2016 | |
| 340 | 25:07.93 | Henry Clay | 2018 | |
| 341 | 25:10.54 | Corbin | 2018 | |
| 342 | 25:12.31 | Lexington Christian | 2018 | |
| 343 | 25:14.63 | Lexington Christian | 2018 | |
| 344 | 25:14.80 | Henry Clay | 2016 | |
| 345 | 25:15.05 | Henry Clay | 2018 | |
| 346 | 25:15.06 | Tates Creek | 2014 | |
| 347 | 25:15.07 | Corbin | 2017 | |
| 348 | 25:15.49 | Lexington Catholic | 2018 | |
| 349 | 25:17.44 | Lafayette | 2016 | |
| 350 | 25:18.41 | North Hardin | 2017 | |
| 351 | 25:19.12 | Garrard County | 2018 | |
| 352 | 25:19.20 | Villa Madonna | 2018 | |
| 353 | 25:19.31 | Tates Creek | 2016 | |
| 354 | 25:23.77 | Grayson County | 2018 | |
| 355 | 25:25.44 | Tates Creek | 2017 | |
| 356 | 25:26.14 | Lloyd Memorial | 2017 | |
| 357 | 25:26.37 | Henry Clay | 2017 | |
| 358 | 25:27.55 | Garrard County | 2018 | |
| 359 | 25:27.80 | Ryle | 2018 | |
| 360 | 25:27.91 | Henry Clay | 2016 | |
| 361 | 25:29.13 | Lafayette | 2017 | |
| 362 | 25:30.03 | Lexington Catholic | 2015 | |
| 363 | 25:30.66 | North Hardin | 2016 | |
| 364 | 25:33.46 | Lexington Catholic | 2017 | |
| 365 | 25:34.03 | Scott County | 2014 | |
| 366 | 25:34.07 | Lloyd Memorial | 2018 | |
| 367 | 25:34.64 | Webster County | 2018 | |
| 368 | 25:35.16 | Webster County | 2016 | |
| 369 | 25:37.68 | Grayson County | 2018 | |
| 370 | 25:37.96 | Lexington Catholic | 2019 | |
| 371 | 25:39.09 | Lafayette | 2018 | |
| 372 | 25:39.51 | Scott County | 2017 | |
| 373 | 25:40.30 | Anderson County | 2017 | |
| 373 | 25:40.30 | Bell County | 2018 | |
| 375 | 25:41.05 | Corbin | 2018 | |
| 376 | 25:42.54 | Lexington Catholic | 2019 | |
| 377 | 25:43.07 | Woodford County | 2015 | |
| 378 | 25:43.55 | Bryan Station | 2019 | |
| 379 | 25:45.48 | Henry Clay | 2017 | |
| 380 | 25:47.55 | Tates Creek | 2015 | |
| 381 | 25:48.66 | Montgomery County | 2019 | |
| 382 | 25:49.04 | Williamsburg | 2015 | |
| 383 | 25:50.10 | Conner | 2018 | |
| 384 | 25:50.70 | Webster County | 2018 | |
| 385 | 25:51.50 | Scott County | 2016 | |
| 386 | 25:52.12 | Ryle | 2017 | |
| 387 | 25:53.34 | Ryle | 2017 | |
| 388 | 25:54.15 | Sayre | 2019 | |
| 389 | 25:55.86 | Bell County | 2019 | |
| 390 | 25:57.95 | Lexington Christian | 2018 | |
| 391 | 26:00.19 | Tates Creek | 2016 | |
| 392 | 26:00.67 | John Hardin | 2019 | |
| 393 | 26:00.72 | Henry Clay | 2019 | |
| 394 | 26:01.16 | Corbin | 2016 | |
| 395 | 26:01.19 | Henry Clay | 2014 | |
| 396 | 26:05.21 | Anderson County | 2015 | |
| 397 | 26:07.30 | Woodford County | 2017 | |
| 398 | 26:07.69 | Henry Clay | 2016 | |
| 399 | 26:10.50 | Bryan Station | 2020 | |
| 400 | 26:10.63 | Lexington Catholic | 2019 | |
| 401 | 26:10.71 | Henry Clay | 2016 | |
| 402 | 26:12.80 | Bell County | 2015 | |
| 403 | 26:14.66 | Bell County | 2019 | |
| 404 | 26:15.13 | Scott County | 2019 | |
| 405 | 26:18.21 | Bryan Station | 2018 | |
| 406 | 26:18.51 | Williamsburg | 2016 | |
| 407 | 26:18.53 | Henry Clay | 2016 | |
| 408 | 26:18.60 | Ryle | 2019 | |
| 409 | 26:20.18 | John Hardin | 2021 | |
| 410 | 26:25.32 | Tates Creek | 2015 | |
| 411 | 26:26.06 | Owen County | 2019 | |
| 412 | 26:27.73 | Lloyd Memorial | 2018 | |
| 413 | 26:31.86 | Ryle | 2016 | |
| 414 | 26:33.76 | Ryle | 2017 | |
| 415 | 26:34.18 | Lexington Catholic | 2018 | |
| 416 | 26:37.35 | Henry Clay | 2018 | |
| 417 | 26:41.07 | Grayson County | 2018 | |
| 418 | 26:43.89 | Henry Clay | 2018 | |
| 419 | 26:44.54 | Corbin | 2018 | |
| 420 | 26:48.51 | Ryle | 2017 | |
| 421 | 26:49.37 | Lexington Catholic | 2017 | |
| 422 | 26:49.42 | Corbin | 2019 | |
| 423 | 26:49.79 | Tates Creek | 2016 | |
| 424 | 26:52.93 | Woodford County | 2019 | |
| 425 | 26:53.32 | Corbin | 2018 | |
| 426 | 26:56.54 | Lexington Catholic | 2017 | |
| 427 | 26:58.30 | Montgomery County | 2019 | |
| 428 | 27:02.43 | Lexington Catholic | 2014 | |
| 429 | 27:04.55 | Owen County | 2020 | |
| 430 | 27:06.22 | Corbin | 2018 | |
| 431 | 27:06.26 | Bryan Station | 2018 | |
| 432 | 27:07.22 | West Jessamine | 2017 | |
| 433 | 27:12.87 | Ryle | 2015 | |
| 434 | 27:16.63 | Ryle | 2017 | |
| 435 | 27:18.89 | Ryle | 2019 | |
| 436 | 27:19.62 | Corbin | 2018 | |
| 437 | 27:19.75 | Bell County | 2018 | |
| 438 | 27:22.74 | Corbin | 2018 | |
| 439 | 27:23.02 | Henry Clay | 2017 | |
| 440 | 27:33.10 | Villa Madonna | 2014 | |
| 441 | 27:35.42 | Henry Clay | 2019 | |
| 442 | 27:38.30 | South Laurel | 2017 | |
| 443 | 27:39.15 | Lafayette | 2015 | |
| 444 | 27:40.47 | Tates Creek | 2019 | |
| 445 | 27:45.39 | Lafayette | 2017 | |
| 446 | 27:46.11 | Lafayette | 2015 | |
| 447 | 27:53.27 | Henry Clay | 2016 | |
| 448 | 27:54.64 | Ryle | 2015 | |
| 449 | 27:56.85 | Williamsburg | 2014 | |
| 450 | 28:00.76 | North Hardin | 2019 | |
| 451 | 28:01.87 | Woodford County | 2018 | |
| 452 | 28:03.04 | Paul Dunbar | 2018 | |
| 453 | 28:04.12 | Henry Clay | 2019 | |
| 454 | 28:06.66 | Henry Clay | 2017 | |
| 455 | 28:07.18 | Henry Clay | 2016 | |
| 456 | 28:07.84 | Conner | 2018 | |
| 457 | 28:12.55 | Bryan Station | 2015 | |
| 458 | 28:13.11 | Henry Clay | 2017 | |
| 459 | 28:14.44 | Corbin | 2016 | |
| 460 | 28:14.93 | Ryle | 2016 | |
| 461 | 28:15.37 | Henry Clay | 2017 | |
| 462 | 28:17.32 | Henry Clay | 2018 | |
| 463 | 28:21.32 | Henry Clay | 2017 | |
| 464 | 28:21.80 | Lexington Catholic | 2018 | |
| 465 | 28:22.94 | Lloyd Memorial | 2016 | |
| 466 | 28:24.40 | North Hardin | 2019 | |
| 467 | 28:28.09 | North Hardin | 2018 | |
| 468 | 28:34.65 | Montgomery County | 2017 | |
| 469 | 28:34.82 | Scott County | 2017 | |
| 470 | 28:37.18 | Lafayette | 2016 | |
| 471 | 28:37.53 | Lafayette | 2019 | |
| 472 | 28:38.93 | Scott County | 2014 | |
| 473 | 28:39.99 | Corbin | 2016 | |
| 474 | 28:41.40 | Lexington Catholic | 2017 | |
| 475 | 28:46.42 | Trimble County | 2017 | |
| 476 | 28:53.31 | Henry Clay | 2017 | |
| 477 | 28:55.46 | Ryle | 2018 | |
| 478 | 28:55.55 | Woodford County | 2017 | |
| 479 | 28:59.23 | Sayre | 2018 | |
| 480 | 29:00.75 | Ryle | 2015 | |
| 481 | 29:14.86 | Corbin | 2018 | |
| 482 | 29:22.28 | Conner | 2019 | |
| 483 | 29:22.51 | North Laurel | 2020 | |
| 484 | 29:22.76 | North Laurel | 2019 | |
| 485 | 29:27.24 | Woodford County | 2017 | |
| 486 | 29:28.11 | Conner | 2018 | |
| 487 | 29:32.54 | North Hardin | 2016 | |
| 488 | 29:34.25 | Grayson County | 2019 | |
| 489 | 29:34.31 | Anderson County | 2015 | |
| 490 | 29:40.78 | Woodford County | 2017 | |
| 491 | 29:41.42 | Henry Clay | 2018 | |
| 492 | 29:45.34 | Bell County | 2019 | |
| 493 | 29:51.55 | Henry Clay | 2018 | |
| 494 | 29:54.43 | Henry Clay | 2019 | |
| 495 | 29:55.02 | Ryle | 2016 | |
| 496 | 30:07.91 | Corbin | 2018 | |
| 497 | 30:10.29 | Bryan Station | 2018 | |
| 498 | 30:11.00 | Ryle | 2018 | |
| 499 | 30:12.32 | Woodford County | 2017 | |
| 500 | 30:14.41 | Ryle | 2018 | |
