| 2068 | 1947 | Marie | Monks | 1241 | F | 38 | 282 | F30-39 | Trumbull | CT | Stratford High School | 58:01 | 55:09 | 17:45 |
| 3291 | 1948 | Magde | Wysocki | 1242 | F | 36 | 283 | F30-39 | | | | 55:10 | 55:10 | 17:46 |
| 2058 | 1949 | Janet | Moffat | 1243 | F | 58 | 201 | F50-59 | Milford | CT | | 1:00:26 | 55:11 | 17:46 |
| 1195 | 1950 | Jillian | Grabowski | 1244 | F | 34 | 284 | F30-39 | Shelton | CT | Victoria Soto School | 1:00:27 | 55:11 | 17:46 |
| 2850 | 1951 | Mackenzie | Snyder | 1245 | F | 13 | 73 | F10-13 | Stratford | CT | | 59:01 | 55:18 | 17:48 |
| 2849 | 1952 | Aiden | Snyder | 705 | M | 15 | 81 | M14-18 | Stratford | CT | | 59:00 | 55:20 | 17:49 |
| 2012 | 1953 | Darlene | Merritt | 1246 | F | 45 | 261 | F40-49 | Stratford | CT | Second Hill Lane Mustangs | 58:33 | 55:20 | 17:49 |
| 3397 | 1954 | Heather | Pucillo | 1247 | F | 50 | 202 | F50-59 | Bridgeport | CT | | 59:04 | 55:20 | 17:49 |
| 3156 | 1955 | Saranika | Vielot | 1248 | F | 31 | 285 | F30-39 | Bridgeport | CT | Determination | 57:40 | 55:20 | 17:49 |
| 3403 | 1956 | Marlo | Gawlak | 1249 | F | 49 | 262 | F40-49 | Seymour | CT | | 57:37 | 55:20 | 17:49 |
| 3402 | 1957 | Kristen | Newall | 1250 | F | 51 | 203 | F50-59 | Shelton | | | 57:36 | 55:21 | 17:49 |
| 467 | 1958 | Katie-Ann | Cervone | 1251 | F | 23 | 247 | F19-29 | Stratford | CT | | 58:34 | 55:21 | 17:49 |
| 2164 | 1959 | Michelle | Nickle | 1252 | F | 30 | 286 | F30-39 | Stratford | CT | | 56:02 | 55:22 | 17:50 |
| 2386 | 1960 | Kristen | Pilley | 1253 | F | 32 | 287 | F30-39 | Bedford | NH | | 56:10 | 55:22 | 17:50 |
| 129 | 1961 | Patricia | Barber | 1254 | F | 52 | 204 | F50-59 | Stratford | CT | | 56:02 | 55:22 | 17:50 |
| 2015 | 1962 | Rachael | Merritt | 1255 | F | 22 | 248 | F19-29 | Stratford | CT | | 58:34 | 55:22 | 17:50 |
| 2525 | 1963 | Diane | Rivera | 1256 | F | 64 | 79 | F60-69 | Bridgeport | CT | Koskoff | 58:58 | 55:23 | 17:50 |
| 1648 | 1964 | Cynthia | Laconte | 1257 | F | 36 | 288 | F30-39 | Hamden | CT | SEASIDE FIT TO THE 9 FITNESS | 1:00:05 | 55:24 | 17:50 |
| 1336 | 1965 | Briana | Hernandez | 1258 | F | 24 | 249 | F19-29 | Meriden | CT | | 55:30 | 55:30 | 17:52 |
| 795 | 1966 | Aimee | Distefano | 1259 | F | 49 | 263 | F40-49 | Stratford | CT | | 58:44 | 55:35 | 17:54 |
| 2124 | 1967 | Kimberly | Murphy | 1260 | F | 50 | 205 | F50-59 | Stratford | CT | | 58:44 | 55:36 | 17:54 |
| 3365 | 1968 | Alexandra | Correa | 1261 | F | 42 | 264 | F40-49 | Stratford | CT | | 1:00:22 | 55:40 | 17:55 |
| 3206 | 1969 | Michelle | Washington | 1262 | F | 49 | 265 | F40-49 | Stratford | CT | Aptar Stratford | 56:16 | 55:45 | 17:57 |
| 4027 | 1970 | Bruce | Lazar | 706 | M | 62 | 56 | M60-69 | Monroe | CT | | 58:59 | 55:45 | 17:57 |
| 1103 | 1971 | Audia | Gayle | 1263 | F | 38 | 289 | F30-39 | Stratford | CT | Aptar Stratford | 56:17 | 55:45 | 17:57 |
| 4028 | 1972 | Diane | Lazar | 1264 | F | 59 | 206 | F50-59 | Monroe | CT | | 58:59 | 55:45 | 17:57 |
| 999 | 1973 | Courtney | Forde | 1265 | F | 35 | 290 | F30-39 | Monroe | CT | Tashua Tigers | 59:05 | 55:47 | 17:58 |
| 2690 | 1974 | Donna | Schaefer | 1266 | F | 54 | 207 | F50-59 | Stratford | CT | | 58:11 | 55:49 | 17:58 |
| 1284 | 1975 | Anne | Hannan | 1267 | F | 55 | 208 | F50-59 | Stratford | CT | | 58:12 | 55:51 | 17:59 |
| 1728 | 1976 | Michael | Lesinsky | 707 | M | 51 | 123 | M50-59 | Stratford | CT | | 57:04 | 55:53 | 17:59 |
| 962 | 1977 | Jessica | Festa | 1268 | F | 42 | 266 | F40-49 | West Haven | CT | St. Mark School | 59:45 | 55:57 | 18:01 |
| 202 | 1978 | Jenna | Bernardo | 1269 | F | 12 | 74 | F10-13 | Stratford | CT | Stratford YMCA | 1:00:15 | 56:00 | 18:02 |
| 3432 | 1979 | Natasha | Feduik | 1270 | F | 41 | 267 | F40-49 | Malverne | NY | | 57:50 | 56:01 | 18:02 |
| 755 | 1980 | Sheetal | Dhawan | 1271 | F | 48 | 268 | F40-49 | Ansonia | CT | CTBraces | 57:58 | 56:02 | 18:02 |
| 3499 | 1981 | Robert | Goetz | 708 | M | 53 | 124 | M50-59 | Stratford | CT | | 57:49 | 56:02 | 18:02 |
| 3431 | 1982 | Lynne | Goetz | 1272 | F | 53 | 209 | F50-59 | Stratford | CT | | 57:49 | 56:02 | 18:02 |
| 1896 | 1983 | Jessica | Martinez | 1273 | F | 32 | 291 | F30-39 | Seymour | CT | CTBraces | 57:58 | 56:02 | 18:03 |
| 1865 | 1984 | Anthony | Marino | 709 | M | 24 | 103 | M19-29 | Derby | CT | CTBraces | 57:57 | 56:02 | 18:03 |
| 4101 | 1985 | Mark | Centopanti | 710 | M | 52 | 125 | M50-59 | Stratford | CT | | 59:29 | 56:03 | 18:03 |
| 149 | 1986 | Mollie | Battista | 1274 | F | 24 | 250 | F19-29 | Bridgeport | CT | | 58:50 | 56:04 | 18:03 |
| 4102 | 1987 | Willi | Centopanti | 1275 | F | 49 | 269 | F40-49 | Stratford | CT | | 59:29 | 56:04 | 18:03 |
| 203 | 1988 | Melissa | Bernardo | 1276 | F | 45 | 270 | F40-49 | Stratford | CT | Stratford YMCA | 1:00:20 | 56:05 | 18:04 |
| 3259 | 1989 | Marianne | Williams | 1277 | F | 54 | 210 | F50-59 | Stratford | CT | | 58:21 | 56:06 | 18:04 |
| 1937 | 1990 | Jamie | Maziarz | 1278 | F | 31 | 292 | F30-39 | Hartford | CT | | 59:03 | 56:07 | 18:04 |
| 3260 | 1991 | Mark | Williams | 711 | M | 57 | 126 | M50-59 | Stratford | CT | | 58:21 | 56:07 | 18:04 |
| 966 | 1992 | Taryn | Figmic | 1279 | F | 25 | 251 | F19-29 | Stratford | CT | | 58:53 | 56:07 | 18:04 |
| 3254 | 1993 | Brendan | Williams | 712 | M | 17 | 82 | M14-18 | Stratford | CT | | 58:20 | 56:07 | 18:04 |
| 2550 | 1994 | Madison | Robotti | 1280 | F | 20 | 252 | F19-29 | Stratford | CT | | 58:53 | 56:07 | 18:04 |
| 2807 | 1995 | Suzanne | Simon | 1281 | F | 59 | 211 | F50-59 | Stratford | CT | Team Imagine | 57:39 | 56:09 | 18:05 |
| 1511 | 1996 | Ryan | Kardamis | 713 | M | 19 | 104 | M19-29 | Stratford | CT | | 58:17 | 56:10 | 18:05 |
| 3076 | 1997 | Mariana | Trovarelli | 1282 | F | 15 | 78 | F14-18 | Stratford | CT | | 58:55 | 56:10 | 18:05 |
| 679 | 1998 | Adriana | Debernardo | 1283 | F | 15 | 79 | F14-18 | Stratford | CT | | 58:55 | 56:11 | 18:05 |
| 2522 | 1999 | Allison | Ritchie | 1284 | F | 50 | 212 | F50-59 | Stratford | CT | Stratford YMCA | 1:00:26 | 56:12 | 18:06 |
| 1509 | 2000 | Beth | Kardamis | 1285 | F | 48 | 271 | F40-49 | Stratford | CT | | 58:18 | 56:12 | 18:06 |
| 1111 | 2001 | Tracy | Gelb | 1286 | F | 45 | 272 | F40-49 | Stratford | CT | | 58:52 | 56:12 | 18:06 |
| 1110 | 2002 | Emma | Gelb | 1287 | F | 7 | 17 | F-9 | Stratford | CT | | 58:52 | 56:13 | 18:06 |
| 3130 | 2003 | Joyce | Varrone | 1288 | F | 66 | 80 | F60-69 | Stratford | CT | | 57:56 | 56:13 | 18:06 |
| 921 | 2004 | Tricia | Farnworth | 1289 | F | 53 | 213 | F50-59 | Wilton | CT | LCDS | 57:01 | 56:13 | 18:06 |
| 477 | 2005 | Denise | Champagne | 1290 | F | 57 | 214 | F50-59 | Stratford | CT | Stratford YMCA | 1:00:27 | 56:14 | 18:06 |
| 2639 | 2006 | Kathy | Sabitsky | 1291 | F | 56 | 215 | F50-59 | Milford | CT | | 57:01 | 56:14 | 18:06 |
| 882 | 2007 | Eleanor | Eng | 1292 | F | 67 | 81 | F60-69 | Stratford | CT | | 57:56 | 56:14 | 18:06 |
| 2572 | 2008 | Lisa | Rodriguez | 1293 | F | 54 | 216 | F50-59 | Stratford | CT | Stratford YMCA | 1:00:27 | 56:15 | 18:07 |
| 2899 | 2009 | Don | Stanziale | 714 | M | 54 | 127 | M50-59 | Shelton | CT | Stanziale | 59:33 | 56:15 | 18:07 |
| 3197 | 2010 | Liz | Wanyo | 1294 | F | 48 | 273 | F40-49 | Stratford | CT | LCDS | 57:03 | 56:15 | 18:07 |
| 2898 | 2011 | Dominique | Stanziale | 1295 | F | 22 | 253 | F19-29 | Shelton | CT | Stanziale | 59:33 | 56:16 | 18:07 |
| 2900 | 2012 | Kim | Stanziale | 1296 | F | 53 | 217 | F50-59 | Shelton | CT | Stanziale | 59:34 | 56:18 | 18:07 |
| 3401 | 2013 | | | 0 | | 0 | 3 | NoData | | | | 57:39 | 56:22 | 18:09 |
| 3289 | 2014 | Nancy | Wright | 1297 | F | 56 | 218 | F50-59 | Naugatuck | CT | | 57:35 | 56:26 | 18:10 |
| 1239 | 2015 | Carrie | Grohs | 1298 | F | 49 | 274 | F40-49 | Naugatuck | CT | | 57:35 | 56:27 | 18:11 |
| 1061 | 2016 | Maryanne | Galardi | 1299 | F | 52 | 219 | F50-59 | Naugatuck | CT | | 57:35 | 56:28 | 18:11 |
| 2636 | 2017 | Lisa | Ryan | 1300 | F | 64 | 82 | F60-69 | Milford | CT | | 57:55 | 56:29 | 18:11 |
| 1986 | 2018 | Michele | McNamara | 1301 | F | 62 | 83 | F60-69 | Stratford | CT | Hillcrest Hawks | 57:55 | 56:29 | 18:11 |
| 75 | 2019 | Michele | Appleby | 1302 | F | 56 | 220 | F50-59 | Stratford | CT | | 57:56 | 56:30 | 18:11 |
| 1360 | 2020 | Beverly | Holt | 1303 | F | 64 | 84 | F60-69 | Stratford | CT | Aptar Stratford | 57:00 | 56:30 | 18:11 |
| 3404 | 2021 | Marissa | Cimino | 1304 | F | 29 | 254 | F19-29 | 06468 | CT | | 57:43 | 56:30 | 18:11 |
| 3399 | 2022 | Jean | Kulas | 1305 | F | 29 | 255 | F19-29 | 06468 | CT | | 57:43 | 56:30 | 18:12 |
| 497 | 2023 | Deanna | Chuka | 1306 | F | 45 | 275 | F40-49 | Trumbull | CT | | 1:00:23 | 56:30 | 18:12 |
| 3273 | 2024 | Jennifer | Winschel | 1307 | F | 61 | 85 | F60-69 | Trumbull | CT | Hillcrest Hawks | 57:55 | 56:31 | 18:12 |
| 498 | 2025 | Wendy | Chuka | 1308 | F | 40 | 276 | F40-49 | Trumbull | CT | | 1:00:24 | 56:31 | 18:12 |
| 4161 | 2026 | Rebecca | Goncalo | 1309 | F | 26 | 256 | F19-29 | Oxford | CT | | 1:00:56 | 56:32 | 18:12 |
| 3359 | 2027 | Lori | Smarz | 1310 | F | 55 | 221 | F50-59 | Oxford | CT | | 58:01 | 56:35 | 18:13 |
| 2501 | 2028 | Dawn | Rice | 1311 | F | 48 | 277 | F40-49 | Wallingford | CT | MULTICULTURAL MAGNET COUGARS | 59:21 | 56:37 | 18:14 |
| 2199 | 2029 | Lori | Obrien | 1312 | F | 52 | 222 | F50-59 | Trumbull | CT | Hillcrest Hawks | 57:55 | 56:38 | 18:14 |
| 2198 | 2030 | Kiley | Obrien | 1313 | F | 22 | 257 | F19-29 | Trumbull | CT | Hillcrest Hawks | 57:55 | 56:39 | 18:14 |
| 3045 | 2031 | Dawn | Tolomeo | 1314 | F | 51 | 223 | F50-59 | Oxford | CT | St. Mark School | 59:28 | 56:39 | 18:14 |
| 3281 | 2032 | Katie | Woessner | 1315 | F | 23 | 258 | F19-29 | Milford | CT | MULTICULTURAL MAGNET COUGARS | 59:23 | 56:39 | 18:14 |
| 511 | 2033 | Jaclyn | Clark | 1316 | F | 9 | 18 | F-9 | | | | 59:28 | 56:39 | 18:14 |
| 513 | 2034 | Melissa | Clark | 1317 | F | 34 | 293 | F30-39 | Stratford | CT | | 59:29 | 56:39 | 18:14 |
| 2457 | 2035 | Kimberly | Quinn | 1318 | F | 49 | 278 | F40-49 | Ansonia | CT | MULTICULTURAL MAGNET COUGARS | 59:23 | 56:39 | 18:14 |
| 2349 | 2036 | Andrea | Peterson | 1319 | F | 49 | 279 | F40-49 | Fairfield | CT | MULTICULTURAL MAGNET COUGARS | 59:24 | 56:40 | 18:15 |
| 512 | 2037 | Jeremy | Clark | 715 | M | 35 | 132 | M30-39 | | | | 59:30 | 56:40 | 18:15 |
| 3079 | 2038 | Leslie | Trudell | 1320 | F | 57 | 224 | F50-59 | Bethel | CT | MULTICULTURAL MAGNET COUGARS | 59:25 | 56:40 | 18:15 |
| 3046 | 2039 | Jordyn | Tolomeo | 1321 | F | 25 | 259 | F19-29 | Oxford | CT | St. Mark School | 59:29 | 56:41 | 18:15 |
| 2028 | 2040 | Breanna | Miller | 1322 | F | 26 | 260 | F19-29 | Stratford | CT | | 59:30 | 56:42 | 18:15 |
| 3225 | 2041 | Kasey | Wendland | 1323 | F | 42 | 280 | F40-49 | Stratford | CT | | 1:00:57 | 56:45 | 18:16 |
| 1171 | 2042 | Danielle | Goncalves | 1324 | F | 40 | 281 | F40-49 | Stratford | CT | | 1:00:56 | 56:45 | 18:16 |
| 3482 | 2043 | Cathy | Hayes | 1325 | F | 53 | 225 | F50-59 | Stratford | CT | | 1:00:23 | 56:46 | 18:16 |
| 1141 | 2044 | Jameson | Gill | 716 | M | 11 | 63 | M10-13 | Stratford | CT | | 59:31 | 56:48 | 18:17 |
| 4024 | 2045 | Sophia | Vazquez | 1326 | F | 10 | 75 | F10-13 | West Hartford | CT | | 59:31 | 56:48 | 18:17 |
| 1142 | 2046 | Liliana | Gill | 1327 | F | 11 | 76 | F10-13 | Stratford | CT | | 59:31 | 56:48 | 18:17 |