Key West, FL
| Rank | Year | Name | Category | Time |
|---|---|---|---|---|
| 1 | 2019 | Brett Sanborn | M 30-39 | 13:20:18 |
| 2 | 2012 | Mike Morton | M 40-49 | 13:42:52 |
| 3 | 2021 | Brett Sanborn | M 30-39 | 14:27:16 |
| 4 | 2014 | Alyson Allen | F 30-39 | 14:42:45 |
| 5 | 2014 | Grant Maughan | M 40-49 | 14:53:04 |
| 6 | 2017 | Marc Burget | M 40-49 | 15:34:22 |
| 7 | 2014 | Traci Falbo | F 40-49 | 15:35:02 |
| 8 | 2014 | Katalin Nagy | F 30-39 | 15:53:13 |
| 9 | 2018 | Zandy Mangold | M 40-49 | 16:05:41 |
| 10 | 2012 | Alyson Allen | F 20-29 | 16:07:06 |
| 11 | 2012 | Tatyana Spencer | F 30-39 | 16:12:57 |
| 12 | 2015 | Vanderley Pereira | M 30-39 | 16:17:01 |
| 13 | 2018 | Szilvia Lubics | F 40-49 | 16:22:15 |
| 14 | 2009 | Brian Krogmann | M | 16:31:10 |
| 15 | 2017 | Don Reichelt | M 30-39 | 16:31:25 |
| 16 | 2018 | Patrick Hrabos | M 30-39 | 16:34:55 |
| 17 | 2014 | Bryce Carlson | M 30-39 | 16:41:42 |
| 18 | 2017 | Ali King | M 30-39 | 16:42:26 |
| 19 | 2022 | Vitor Rodrigues | M 30-39 | 16:42:34 |
| 20 | 2012 | Neal Lucas | M 20-29 | 16:42:39 |
| 21 | 2015 | Grant Maughan | M 50-59 | 16:52:56 |
| 22 | 2019 | Patrick Hrabos | M 30-39 | 16:52:59 |
| 23 | 2021 | Oz Pearlman | M 30-39 | 16:53:25 |
| 24 | 2021 | Cole Bataille | M 30-39 | 16:57:52 |
| 25 | 2012 | Sung Ho Choi | M 30-39 | 17:00:29 |
| 26 | 2014 | George Myers | M 40-49 | 17:09:00 |
| 27 | 2010 | Jonathan Savage | M | 17:14:04 |
| 28 | 2013 | Brenda Carawan | F 30-39 | 17:16:20 |
| 29 | 2017 | Micah Morgan | F 30-39 | 17:20:00 |
| 30 | 2019 | Oz Pearlman | M 30-39 | 17:22:22 |
| 31 | 2013 | Dave Krupski | M 30-39 | 17:30:45 |
| 32 | 2014 | Daniel OrLek | M 40-49 | 17:31:36 |
| 33 | 2014 | Dave Krupski | M 30-39 | 17:38:06 |
| 34 | 2018 | Jake Rankinen | M 30-39 | 17:45:02 |
| 35 | 2014 | Andy Woods | M 40-49 | 17:45:27 |
| 36 | 2021 | Liza Howard | F 40-49 | 17:49:34 |
| 37 | 2011 | Dave Carver | M 40-49 | 17:51:19 |
| 38 | 2018 | Bojan Maric | M 40-49 | 17:52:38 |
| 39 | 2017 | Ronnie Delzer | M 30-39 | 17:53:47 |
| 40 | 2021 | Mark Wooten | M 40-49 | 17:54:18 |
| 41 | 2013 | Andrei Nana | M 30-39 | 17:54:55 |
| 42 | 2015 | Byron Roca | M 20-29 | 18:14:31 |
| 43 | 2015 | Dave Krupski | M 30-39 | 18:16:37 |
| 44 | 2013 | Josephine Weeden | F 40-49 | 18:17:00 |
| 45 | 2023 | Andy Day | M 50-59 | 18:20:35 |
| 46 | 2011 | Joe Ninke | M 40-49 | 18:22:46 |
| 47 | 2016 | Alyson Allen | F 30-39 | 18:27:35 |
| 48 | 2019 | Igor Gotsuliak | M 30-39 | 18:29:53 |
| 49 | 2014 | Chris Benjamin | M 30-39 | 18:30:48 |
| 50 | 2017 | Michael Runyon | M 20-29 | 18:31:34 |
| 51 | 2018 | Mika Thewes | F 20-29 | 18:32:30 |
| 52 | 2017 | Robert Tagher | M 40-49 | 18:35:12 |
| 53 | 2010 | Jennifer Vogel | F | 18:37:00 |
| 54 | 2012 | Dave Krupski | M 30-39 | 18:38:48 |
| 55 | 2014 | Dan McHugh | M 40-49 | 18:41:06 |
| 56 | 2019 | Lori Mitchener | F 40-49 | 18:41:16 |
| 57 | 2017 | Steven Carr | M 50-59 | 18:44:14 |
| 58 | 2021 | Jessica Jones | F 40-49 | 18:44:50 |
| 59 | 2013 | Grant Maughan | M 40-49 | 18:45:22 |
| 60 | 2018 | Brett Faulknier | M 40-49 | 18:47:40 |
| 61 | 2017 | Nancy Levene | F 40-49 | 18:48:50 |
| 62 | 2019 | Michael Ryan | M 40-49 | 18:50:12 |
| 63 | 2021 | Hans Van Zanten | M 40-49 | 18:53:57 |
| 64 | 2022 | Brian Million | M 40-49 | 18:54:48 |
| 65 | 2021 | Lisa Devona | F 40-49 | 19:01:48 |
| 66 | 2013 | Joe Lee | M 50-59 | 19:10:04 |
| 67 | 2009 | Jennifer Vogel | F | 19:10:33 |
| 68 | 2023 | Jessica Jones | F 40-49 | 19:11:51 |
| 69 | 2014 | Brett Sobieraski | M 40-49 | 19:12:06 |
| 70 | 2017 | Grant Maughan | M 50-59 | 19:15:16 |
| 71 | 2016 | Cortland Wheeler | M 20-29 | 19:16:15 |
| 72 | 2012 | Bradford Lombardi | M 40-49 | 19:19:30 |
| 73 | 2018 | Chris McCarthy | M 30-39 | 19:20:25 |
| 74 | 2014 | Gigi Tsang | F 40-49 | 19:27:54 |
| 75 | 2017 | Andrew Farretta | M 30-39 | 19:31:04 |
| 76 | 2011 | Pam Reed | F 50-59 | 19:32:19 |
| 77 | 2013 | Sung Ho Choi | M 30-39 | 19:32:26 |
| 78 | 2010 | Joe Ninke | M | 19:33:26 |
| 79 | 2014 | Jonathan Savage | M 40-49 | 19:35:33 |
| 80 | 2018 | Brian Hill | M 40-49 | 19:37:47 |
| 81 | 2011 | Lane Vogel | M 30-39 | 19:38:12 |
| 82 | 2023 | Caryn Lubetsky | F 50-59 | 19:39:00 |
| 83 | 2014 | Chris Roman | M 40-49 | 19:42:08 |
| 84 | 2018 | Derek Dowell | M 30-39 | 19:43:19 |
| 85 | 2022 | Caryn Lubetsky | F 50-59 | 19:43:52 |
| 86 | 2017 | Noelani Taylor | F 30-39 | 19:44:39 |
| 87 | 2013 | Maggie Beach | F 40-49 | 19:44:39 |
| 88 | 2009 | Diana Widdowson | F | 19:44:46 |
| 89 | 2019 | Luis Gomez | M 30-39 | 19:45:25 |
| 90 | 2019 | Megan Alvarado | F 30-39 | 19:50:20 |
| 91 | 2022 | Jessica Jones | F 40-49 | 19:53:24 |
| 92 | 2014 | Byron Roca | M 20-29 | 19:53:25 |
| 93 | 2021 | Nancy Levene | F 50-59 | 19:55:07 |
| 94 | 2015 | Zandy Mangold | M 40-49 | 19:55:34 |
| 95 | 2015 | Will Glover | M 40-49 | 19:55:52 |
| 96 | 2019 | Grant Maughan | M 50-59 | 19:56:46 |
| 97 | 2016 | Dan McHugh | M 40-49 | 20:00:54 |
| 98 | 2018 | Rich Flint | M 50-59 | 20:01:25 |
| 99 | 2019 | Nancy Levene | F 50-59 | 20:10:19 |
| 100 | 2018 | Gilberto Toigo | M 50-59 | 20:11:00 |
