| 2434 | 2006 | Sara | Petrucelli | 1251 | F | 33 | 253 | F3039 | Shelton | CT | LONG LOTS SCHOOL | 54:31 | 51:37 | 16:37 |
| 1252 | 2007 | Linda | Gullotta | 1252 | F | 56 | 157 | F5059 | Bridgeport | CT | TEAM KOSKOFF | 54:35 | 51:38 | 16:37 |
| 510 | 2008 | Amy | CiccaglioneBarden | 1253 | F | 32 | 254 | F3039 | Trumbull | CT | PEDIATRIC HEALTHCARE ASSOCIATES | 53:53 | 51:38 | 16:38 |
| 2967 | 2009 | Erika | Soto | 1254 | F | 32 | 255 | F3039 | Bridgeport | CT | | 53:59 | 51:40 | 16:38 |
| 3773 | 2010 | Samantha | Peters | 1255 | F | 19 | 274 | F1929 | Monroe | CT | | 56:54 | 51:41 | 16:38 |
| 3774 | 2011 | Ceira | Monahan | 1256 | F | 19 | 275 | F1929 | Kingston | MA | | 56:54 | 51:41 | 16:39 |
| 1922 | 2012 | Jennifer | Martinez | 1257 | F | 30 | 256 | F3039 | Shelton | CT | | 54:03 | 51:42 | 16:39 |
| 3260 | 2013 | Sarah | Voccola | 1258 | F | 54 | 158 | F5059 | Stratford | CT | STRATFORD HIGH SCHOOL | 56:54 | 51:42 | 16:39 |
| 1709 | 2014 | Diane | Lawlor | 1259 | F | 62 | 66 | F6069 | Ansonia | CT | PJ'S PALS | 53:31 | 51:44 | 16:39 |
| 1997 | 2015 | Peggy | McGowan | 1260 | F | 65 | 67 | F6069 | Ansonia | CT | PJ'S PALS | 53:31 | 51:44 | 16:40 |
| 942 | 2016 | Chris | Farrell | 755 | M | 44 | 148 | M4049 | Stratford | CT | ELI WHITNEY | 55:47 | 51:47 | 16:40 |
| 2523 | 2017 | Jenna | Quagliaroli | 1261 | F | 25 | 276 | F1929 | Wallingford | CT | | 55:37 | 51:48 | 16:41 |
| 22 | 2018 | Max | Agathos | 756 | M | 9 | 21 | M-9 | Stratford | CT | | 55:48 | 51:49 | 16:41 |
| 192 | 2019 | Emily | Benson | 1262 | F | 27 | 277 | F1929 | Wallingford | CT | | 55:37 | 51:49 | 16:41 |
| 21 | 2020 | Chris | Agathos | 757 | M | 43 | 149 | M4049 | Stratford | CT | | 55:50 | 51:50 | 16:41 |
| 788 | 2021 | Antonio | Dimatteo | 758 | M | 41 | 150 | M4049 | Stratford | CT | ST MARK SCHOOL | 55:57 | 51:53 | 16:42 |
| 3157 | 2022 | Amina | Toor | 1263 | F | 28 | 278 | F1929 | Stamford | CT | STRAWBERRY HILL | 55:55 | 51:56 | 16:43 |
| 3102 | 2023 | Ryan | Tayman | 759 | M | 41 | 151 | M4049 | Stratford | CT | ST MARK SCHOOL | 55:57 | 51:56 | 16:43 |
| 2239 | 2024 | Julianna | Nunez | 1264 | F | 17 | 104 | F1418 | Stratford | CT | | 52:22 | 51:56 | 16:43 |
| 3270 | 2025 | Jeannie | Wade | 1265 | F | 60 | 68 | F6069 | Trumbull | CT | | 55:43 | 51:59 | 16:44 |
| 1308 | 2026 | Jennifer | Hawkins | 1266 | F | 40 | 265 | F4049 | Stratford | CT | NEW ENGLAND BALLET COMPANY | 55:07 | 52:00 | 16:45 |
| 2189 | 2027 | Rosann | Nawrocki | 1267 | F | 46 | 266 | F4049 | Stratford | CT | JOHNSON TIGERS. | 55:35 | 52:01 | 16:45 |
| 3251 | 2028 | Barbara | Vitka | 1268 | F | 49 | 267 | F4049 | Stratford | CT | | 55:35 | 52:01 | 16:45 |
| 2960 | 2029 | Natalie | Somley | 1269 | F | 52 | 159 | F5059 | Monroe | CT | | 52:17 | 52:03 | 16:45 |
| 2838 | 2030 | Lisa | Seperack | 1270 | F | 48 | 268 | F4049 | Stratford | CT | SEP BOYS | 55:35 | 52:03 | 16:45 |
| 3289 | 2031 | Emma | Walter | 1271 | F | 17 | 105 | F1418 | Wilton | CT | WILTON HIGH SCHOOL GERMAN HONOR | 54:04 | 52:03 | 16:46 |
| 588 | 2032 | Jeffrey | Correia | 760 | M | 59 | 114 | M5059 | Milford | CT | TEAM VICKI | 57:50 | 52:03 | 16:46 |
| 3301 | 2033 | Tyler | Warren | 761 | M | 17 | 87 | M1418 | Wilton | CT | WILTON HIGH SCHOOL GERMAN HONOR | 54:03 | 52:05 | 16:46 |
| 958 | 2034 | Angela | Fazio | 1272 | F | 58 | 160 | F5059 | Norwalk | CT | TRACEY SCHOOL | 57:16 | 52:05 | 16:46 |
| 959 | 2035 | Christopher | Fazio | 762 | M | 61 | 41 | M6069 | Norwalk | CT | TRACEY SCHOOL | 57:16 | 52:07 | 16:47 |
| 38 | 2036 | Carley | Altemose | 1273 | F | 24 | 279 | F1929 | Stratford | CT | NORTHWEST 7 | 56:15 | 52:07 | 16:47 |
| 2767 | 2037 | Joan | Saravia | 1274 | F | 34 | 257 | F3039 | Bridgeport | CT | CT BRACES | 54:28 | 52:10 | 16:48 |
| 3305 | 2038 | Ella | Wassmann | 1275 | F | 14 | 106 | F1418 | Stratford | CT | STRATFORD HIGH SCHOOL | 55:39 | 52:11 | 16:48 |
| 2533 | 2039 | Kayla | Quirk | 1276 | F | 14 | 107 | F1418 | Stratford | CT | | 55:39 | 52:13 | 16:49 |
| 124 | 2040 | Natalie | Baldowski | 1277 | F | 13 | 103 | F1013 | Stratford | CT | FLOOD MIDDLE SCHOOL CROSS COUNTR | 54:08 | 52:14 | 16:49 |
| 2095 | 2041 | Nicole | Morales | 1278 | F | 31 | 258 | F3039 | Bridgeport | CT | CT BRACES | 54:27 | 52:14 | 16:49 |
| 3059 | 2042 | Ryanne | Mariano | 1279 | F | 12 | 104 | F1013 | Stratford | CT | | 54:08 | 52:15 | 16:49 |
| 513 | 2043 | Larry | Ciccarelli | 763 | M | 58 | 115 | M5059 | Stratford | CT | ZAIN | 55:19 | 52:15 | 16:49 |
| 3536 | 2044 | Cindy | Buynovsky | 1280 | F | 53 | 161 | F5059 | Stratford | CT | | 53:52 | 52:16 | 16:50 |
| 1623 | 2045 | Melanie | Koonitsky | 1281 | F | 49 | 269 | F4049 | Stratford | CT | ST MARK SCHOOL | 56:00 | 52:16 | 16:50 |
| 3354 | 2046 | Aneequa | William | 1282 | F | 30 | 259 | F3039 | Bridgeport | CT | CT BRACES | 54:27 | 52:17 | 16:50 |
| 1198 | 2047 | Valerie | Gonzalez | 1283 | F | 28 | 280 | F1929 | Bridgeport | CT | CT BRACES | 54:27 | 52:17 | 16:50 |
| 1390 | 2048 | Jennifer | Hoynes | 1284 | F | 46 | 270 | F4049 | Stratford | CT | LORDSHIP | 55:59 | 52:18 | 16:50 |
| 1439 | 2049 | Jerika | M.Izcoa | 1285 | F | 32 | 260 | F3039 | Stratford | CT | NO | 54:03 | 52:18 | 16:50 |
| 3344 | 2050 | Suzanne | Whittaker | 1286 | F | 37 | 261 | F3039 | North Haven | CT | ANSONIA SCHOOLS | 52:30 | 52:18 | 16:50 |
| 514 | 2051 | Marli | Ciccarelli | 1287 | F | 35 | 262 | F3039 | Milford | CT | | 55:22 | 52:18 | 16:50 |
| 2958 | 2052 | Emma | Solomon | 1288 | F | 15 | 108 | F1418 | Stratford | CT | | 57:11 | 52:18 | 16:50 |
| 512 | 2053 | Larry | Ciccarelli | 764 | M | 35 | 140 | M3039 | Milford | CT | | 55:23 | 52:19 | 16:51 |
| 1032 | 2054 | Kris | Forsythe | 1289 | F | 51 | 162 | F5059 | Shelton | CT | TEAMJAN | 57:41 | 52:20 | 16:51 |
| 396 | 2055 | Sarah | Calzone | 1290 | F | 35 | 263 | F3039 | Stratford | CT | | 54:04 | 52:21 | 16:51 |
| 404 | 2056 | Corrin | Cannon | 1291 | F | 28 | 281 | F1929 | Stratford | CT | | 57:22 | 52:21 | 16:51 |
| 2195 | 2057 | Carrie | Negron | 1292 | F | 40 | 271 | F4049 | Stratford | CT | | 55:51 | 52:21 | 16:51 |
| 1108 | 2058 | Danielle | Gaspar | 1293 | F | 28 | 282 | F1929 | Stratford | CT | | 57:22 | 52:21 | 16:51 |
| 2196 | 2059 | Luis | Negron | 765 | M | 41 | 152 | M4049 | Stratford | CT | | 55:51 | 52:22 | 16:52 |
| 3098 | 2060 | Ashlynn | Taylor | 1294 | F | 11 | 105 | F1013 | Stratford | CT | ELI WHITNEY | 57:13 | 52:22 | 16:52 |
| 491 | 2061 | Jimmy | Chaves | 766 | M | 38 | 141 | M3039 | Stratford | CT | | 58:18 | 52:25 | 16:52 |
| 1642 | 2062 | Rick | Kretvix | 767 | M | 49 | 153 | M4049 | Stratford | CT | | 54:41 | 52:25 | 16:52 |
| 1750 | 2063 | Meghan | Letko | 1295 | F | 37 | 264 | F3039 | Stratford | CT | | 58:04 | 52:25 | 16:53 |
| 3624 | 2064 | Erin | Wojdaszka | 1296 | F | 38 | 265 | F3039 | Stratford | CT | | 58:06 | 52:26 | 16:53 |
| 549 | 2065 | Frances | Cole | 1297 | F | 62 | 69 | F6069 | Monroe | CT | | 53:54 | 52:26 | 16:53 |
| 1785 | 2066 | Alan | Llewelyn | 768 | M | 46 | 154 | M4049 | Stratford | CT | DARIEN TEACHERS | 55:10 | 52:26 | 16:53 |
| 1787 | 2067 | Kate | Llewelyn | 1298 | F | 53 | 163 | F5059 | Stratford | CT | DARIEN TEACHERS | 55:10 | 52:26 | 16:53 |
| 1052 | 2068 | Gary | Frankel | 769 | M | 48 | 155 | M4049 | Derby | CT | | 54:40 | 52:28 | 16:54 |
| 3052 | 2069 | Deirdre | Sulllivan | 1299 | F | 47 | 272 | F4049 | Milford | CT | TEAMJAN | 57:41 | 52:32 | 16:55 |
| 3499 | 2070 | Julia | Perez | 1300 | F | 38 | 266 | F3039 | Bethany | CT | | 54:20 | 52:33 | 16:55 |
| 1360 | 2071 | Andrea | Hodska | 1301 | F | 74 | 3 | F7079 | Stratford | CT | DRAGONFLIES | 53:44 | 52:35 | 16:56 |
| 797 | 2072 | Suzanne | Dimenna | 1302 | F | 56 | 164 | F5059 | Huntington | CT | | 57:50 | 52:40 | 16:57 |
| 3402 | 2073 | Devan | Yoder | 1303 | F | 27 | 283 | F1929 | Norwalk | CT | JEFFERSON | 59:18 | 52:42 | 16:58 |
| 2806 | 2074 | Carolyn | Schuler | 1304 | F | 35 | 267 | F3039 | East Haven | CT | NORWALK TEACHERS | 59:19 | 52:43 | 16:59 |
| 3381 | 2075 | Jennifer | Woods | 1305 | F | 45 | 273 | F4049 | Fairfield | CT | NORWALK TEACHERS | 59:19 | 52:44 | 16:59 |
| 256 | 2076 | Armando | Bolivar | 770 | M | 43 | 156 | M4049 | Bridgeport | CT | TEAM SANTA | 54:02 | 52:44 | 16:59 |
| 3475 | 2077 | Amy | Piercy | 1306 | F | 50 | 165 | F5059 | Louiseville | KY | | 54:29 | 52:44 | 16:59 |
| 3476 | 2078 | Michelle | Lecardo | 1307 | F | 49 | 274 | F4049 | Stratford | CT | | 54:28 | 52:45 | 16:59 |
| 257 | 2079 | Lucy | Bolivar | 1308 | F | 47 | 275 | F4049 | Bridgeport | CT | TEAM SANTA | 54:02 | 52:45 | 16:59 |
| 1760 | 2080 | Emily | Levine | 1309 | F | 29 | 284 | F1929 | Bridgeport | CT | CT BRACES | 53:35 | 52:45 | 16:59 |
| 2710 | 2081 | Arianna | Rouse | 1310 | F | 11 | 106 | F1013 | Stratford | CT | ST MARK SCHOOL | 55:58 | 52:45 | 16:59 |
| 3112 | 2082 | Lynn | Terry | 1311 | F | 51 | 166 | F5059 | Westport | CT | | 55:12 | 52:45 | 16:59 |
| 2661 | 2083 | Megan | Rodriguez | 1312 | F | 35 | 268 | F3039 | Oxford | CT | DARIEN TEACHERS | 58:42 | 52:46 | 16:59 |
| 3393 | 2084 | David | Wrinn | 771 | M | 55 | 116 | M5059 | Norwalk | CT | SEDONA SIX | 58:42 | 52:46 | 16:59 |
| 3794 | 2085 | Sara | Nelson | 1313 | F | 26 | 285 | F1929 | Norwalk | CT | | 58:42 | 52:46 | 16:59 |
| 616 | 2086 | Lindsay | Cruickshank | 1314 | F | 25 | 286 | F1929 | Norwalk | CT | DARIEN TEACHERS | 58:42 | 52:46 | 16:59 |
| 3682 | 2087 | Melissa | Ortiz | 1315 | F | 35 | 269 | F3039 | Norwalk | CT | | 59:18 | 52:47 | 17:00 |
| 840 | 2088 | Anne | Doucette | 1316 | F | 55 | 167 | F5059 | Fairfield | CT | | 55:02 | 52:49 | 17:00 |
| 865 | 2089 | Ryan | Duffy | 772 | M | 18 | 88 | M1418 | Stratford | CT | | 55:27 | 52:50 | 17:01 |
| 2575 | 2090 | Ave | Reilly | 1317 | F | 16 | 109 | F1418 | Stratford | CT | STRATFORD HIGH SCHOOL GIRLS SOCC | 58:23 | 52:51 | 17:01 |
| 3474 | 2091 | Johanna | Izcoa | 1318 | F | 13 | 107 | F1013 | Stratford | CT | | 54:48 | 52:54 | 17:02 |
| 1003 | 2092 | Ashlyn | Flaig | 1319 | F | 9 | 13 | F-9 | Stratford | CT | ST MARK SCHOOL | 56:07 | 52:55 | 17:02 |
| 2422 | 2093 | Kaitlin | Petrella | 1320 | F | 29 | 287 | F1929 | Bridgeport | CT | BEDFORD MS BEARS | 55:19 | 52:55 | 17:02 |
| 975 | 2094 | Laura | Ferrarese | 1321 | F | 26 | 288 | F1929 | Fairfield | CT | | 55:41 | 52:56 | 17:02 |
| 1864 | 2095 | Brittany | Man | 1322 | F | 30 | 270 | F3039 | Monroe | CT | | 55:42 | 52:56 | 17:02 |
| 1793 | 2096 | Christie | Lombardi | 1323 | F | 29 | 289 | F1929 | West Hartford | CT | BEDFORD MS BEARS | 55:20 | 52:56 | 17:02 |
| 129 | 2097 | Danielle | Barberi | 1324 | F | 25 | 290 | F1929 | Trumbull | CT | | 56:08 | 52:56 | 17:02 |
| 1130 | 2098 | Helena | Gerardi | 1325 | F | 18 | 110 | F1418 | Stratford | CT | | 55:57 | 52:56 | 17:03 |
| 3478 | 2099 | Courtney | Lecardo | 1326 | F | 13 | 108 | F1013 | Stratford | CT | | 54:49 | 52:57 | 17:03 |
| 1796 | 2100 | Matthew | Lombardi | 773 | M | 33 | 142 | M3039 | West Hartford | CT | BEDFORD MS BEARS | 55:20 | 52:57 | 17:03 |
| 2906 | 2101 | John | Simon | 774 | M | 43 | 157 | M4049 | Shelton | CT | LORDSHIP COMMUNITY CHURCH | 57:19 | 52:57 | 17:03 |
| 1133 | 2102 | Michael | Gerardi | 775 | M | 57 | 117 | M5059 | Stratford | CT | | 55:57 | 52:57 | 17:03 |
| 3784 | 2103 | Melissa | Jacob | 1327 | F | 43 | 276 | F4049 | Shelton | CT | | 55:06 | 53:01 | 17:04 |
| 1273 | 2104 | Shelby | Halliday | 1328 | F | 24 | 291 | F1929 | Fairfield | CT | FAIRFIELD PUBLIC SCHOOLS | 57:31 | 53:01 | 17:04 |
| 3721 | 2105 | Sandy | Bremer | 1329 | F | 54 | 168 | F5059 | Fairfield | CT | | 57:31 | 53:01 | 17:04 |