Key West, FL
| Rank | Year | Name | Category | Time |
|---|---|---|---|---|
| 1 | 2015 | David Kilgore | M 20-29 | 4:19:17 |
| 2 | 2021 | Jeff Welsh | M 30-39 | 4:26:21 |
| 3 | 2021 | Michael Neel | M 30-39 | 4:30:10 |
| 4 | 2016 | Alice Henley | F 20-29 | 4:33:35 |
| 5 | 2016 | Lauren Hendrix | F 30-39 | 4:36:11 |
| 6 | 2018 | James Nelson | M 50-59 | 4:37:00 |
| 7 | 2017 | James Nelson | M 50-59 | 4:44:53 |
| 8 | 2019 | Nicholas Heath | M 20-29 | 4:46:04 |
| 9 | 2022 | Jeff Welsh | M 30-39 | 4:49:01 |
| 10 | 2019 | James Nelson | M 50-59 | 4:55:03 |
| 11 | 2019 | Nikolay Ryabkov | M 30-39 | 4:55:37 |
| 12 | 2019 | Bob Hoogendoorn | M 20-29 | 4:56:09 |
| 13 | 2016 | James Nelson | M 50-59 | 4:57:30 |
| 14 | 2023 | Zachary Evans | M 30-39 | 4:58:23 |
| 15 | 2023 | Bruno Greppi | M 50-59 | 5:09:30 |
| 16 | 2017 | Terese Moya | F 30-39 | 5:14:39 |
| 17 | 2019 | Danielle Witkowski | F 40-49 | 5:14:55 |
| 18 | 2022 | Alex Shtogren | M 40-49 | 5:21:00 |
| 19 | 2018 | Francisco Alvarez | M 40-49 | 5:21:25 |
| 20 | 2017 | Sara Medrano | F 40-49 | 5:21:28 |
| 21 | 2019 | Judd Lorson | M 30-39 | 5:22:17 |
| 22 | 2018 | Ruben Veliz | M 40-49 | 5:22:58 |
| 23 | 2021 | Parnian Hernandez | F 30-39 | 5:24:15 |
| 24 | 2021 | Adriana McGrath | F 50-59 | 5:28:36 |
| 25 | 2023 | James Nelson | M 50-59 | 5:28:42 |
| 26 | 2018 | Greg Fender | M 50-59 | 5:30:11 |
| 27 | 2023 | Charles Heaton | M 40-49 | 5:30:17 |
| 28 | 2021 | Nancy A | F 40-49 | 5:30:44 |
| 29 | 2018 | Chris Williams | M 40-49 | 5:32:34 |
| 30 | 2018 | Jose Lim | M 60-69 | 5:35:22 |
| 31 | 2017 | Chris Williams | M 40-49 | 5:37:52 |
| 32 | 2022 | Belen Coronel | F 30-39 | 5:38:37 |
| 33 | 2015 | Fabiola Morales | F 30-39 | 5:39:56 |
| 34 | 2015 | Caitlin Lopez | F < 20 | 5:40:13 |
| 35 | 2022 | Luis Cocco | M 40-49 | 5:42:10 |
| 36 | 2015 | Rafael Caballero | M 30-39 | 5:43:16 |
| 37 | 2017 | Miguel Gonzalez | M 20-29 | 5:45:32 |
| 38 | 2016 | Andrew Farretta | M 30-39 | 5:46:02 |
| 39 | 2022 | Andrew Cortez | M 50-59 | 5:46:11 |
| 40 | 2015 | Freddy Goldszmidt | M 50-59 | 5:46:17 |
| 41 | 2015 | Rolando Barberis | M 40-49 | 5:48:55 |
| 42 | 2017 | Nicole Naquin | F 30-39 | 5:50:49 |
| 43 | 2017 | David Moss | M 40-49 | 5:51:05 |
| 44 | 2021 | Brian Detweiler | M 30-39 | 5:51:36 |
| 45 | 2015 | Hector Arana | M 40-49 | 5:52:29 |
| 46 | 2018 | April Reber | F 30-39 | 5:55:23 |
| 47 | 2017 | Lucia Havlovic | F 30-39 | 5:57:08 |
| 48 | 2021 | Jose Ignacio Perez | M 30-39 | 5:59:04 |
| 49 | 2023 | Whitney Dancaster | F 30-39 | 6:00:08 |
| 50 | 2022 | Sarah Raaymakers | F 30-39 | 6:00:24 |
| 51 | 2019 | Michael Bond | M 30-39 | 6:00:40 |
| 52 | 2021 | Whitney Dancaster | F 30-39 | 6:02:35 |
| 53 | 2017 | Sarah Williams | F 40-49 | 6:03:13 |
| 54 | 2018 | Chad Dill | M 40-49 | 6:03:39 |
| 55 | 2021 | David Diffenbach | M 50-59 | 6:05:20 |
| 56 | 2015 | Alexandra St Pierre | F 20-29 | 6:06:08 |
| 57 | 2018 | Tracy Racich | F 40-49 | 6:06:39 |
| 58 | 2017 | Rowland Francisco | M 20-29 | 6:07:02 |
| 59 | 2017 | Dawn Forman-Lisenby | F 40-49 | 6:08:08 |
| 60 | 2019 | Jackson Alfaro | M 30-39 | 6:08:45 |
| 61 | 2019 | Brian Detweiler | M 30-39 | 6:11:42 |
| 62 | 2018 | Marcos Ferreira | M 30-39 | 6:11:53 |
| 63 | 2015 | Mandy Miller | F 50-59 | 6:12:37 |
| 64 | 2017 | Joseph McCann | M 30-39 | 6:12:46 |
| 65 | 2021 | Forrest Rose | M 30-39 | 6:13:17 |
| 66 | 2015 | Linda Sanders | F 40-49 | 6:13:26 |
| 67 | 2022 | Allan Perez | M 60-69 | 6:13:41 |
| 68 | 2018 | Graham de Gottal | M 50-59 | 6:14:06 |
| 69 | 2017 | Theresa Gusman | F 50-59 | 6:16:38 |
| 70 | 2019 | Rebecca Rybicki | F 30-39 | 6:17:47 |
| 71 | 2018 | Rob Maffeo | M 40-49 | 6:19:07 |
| 72 | 2018 | Whitney Dancaster | F 20-29 | 6:19:39 |
| 73 | 2022 | Stuart Masch | M 60-69 | 6:20:56 |
| 74 | 2019 | Michael Stork | M 40-49 | 6:21:18 |
| 75 | 2018 | Jamie Moger | M 40-49 | 6:22:19 |
| 76 | 2016 | Chris Williams | M 40-49 | 6:23:39 |
| 77 | 2019 | Dawn Forman-Lisenby | F 50-59 | 6:24:29 |
| 78 | 2022 | Sarah Williams | F 40-49 | 6:24:40 |
| 79 | 2019 | Stuart Masch | M 60-69 | 6:25:43 |
| 80 | 2015 | Alan Benenson | M 40-49 | 6:27:48 |
| 81 | 2018 | Brittany Estes | F 30-39 | 6:28:13 |
| 82 | 2021 | Cheryl Wright | F 50-59 | 6:30:06 |
| 83 | 2019 | Samantha Kornely | F 40-49 | 6:30:45 |
| 84 | 2018 | Rachel Quad | F 20-29 | 6:31:26 |
| 85 | 2022 | Lynn Crossman | F 40-49 | 6:31:34 |
| 86 | 2017 | Patricia Shapiro | F 60-69 | 6:31:47 |
| 87 | 2017 | Kattia Sanchez-Maroto | F 40-49 | 6:31:53 |
| 88 | 2016 | Kareen Lyn | F 40-49 | 6:32:00 |
| 89 | 2019 | Maurice Matthews | M 30-39 | 6:32:17 |
| 90 | 2016 | Cuche Alarcon | M 40-49 | 6:33:14 |
| 91 | 2019 | Neil Blethyn | M 40-49 | 6:33:42 |
| 92 | 2019 | Steve Butler | M 30-39 | 6:33:42 |
| 93 | 2018 | Brendan Barry | M 50-59 | 6:33:53 |
| 94 | 2017 | Matthew Lapaglia | M 30-39 | 6:34:25 |
| 95 | 2017 | Jacob Mays | M 20-29 | 6:34:39 |
| 96 | 2021 | Tuan Nguyen | M 30-39 | 6:34:45 |
| 97 | 2017 | Tracy Racich | F 40-49 | 6:36:01 |
| 98 | 2021 | Matthew Sibert | M 30-39 | 6:36:41 |
| 99 | 2018 | Ilinke Royse | F 40-49 | 6:36:52 |
| 100 | 2018 | Tina Wingard | F 30-39 | 6:36:52 |
