 | Ray Einig | Sunday, August 25, 2024 Chicago Triathlon | (triathlon) | 3:11:34 | 1,016th Place Male 33rd Place (M 55-59) | |
 | Volker Rose | Sunday, August 25, 2024 Chicago Triathlon | (triathlon) | 1:23:00 |  M 55-59 | |
 | Volker Rose | Sunday, August 27, 2023 Chicago Triathlon | (triathlon) | 1:08:04 |  M 50-54 | |
 | Cherish Hairrell | Sunday, August 29, 2021 Chicago Triathlon | (triathlon) | 1:47:50 | 120th Place Female 5th Place (F 55-59) | |
 | Cherish Hairrell | Sunday, August 25, 2019 Chicago Triathlon | (triathlon) | 1:29:38 | 143rd Place Female 9th Place (F 50-54) | |
 | Ray Einig | Sunday, August 25, 2019 Chicago Triathlon | (triathlon) | 1:35:30 | 698th Place Male 26th Place (M 50-54) | |
 | Jonathan Cain | Sunday, August 27, 2017 Chicago Triathlon | (triathlon) | 1:30:52 | 128th Place Male 12th Place (M 35-39) | |
 | Cherish Hairrell | Sunday, August 27, 2017 Chicago Triathlon | (triathlon) | 1:41:27 | 109th Place Female 6th Place (F 50-54) | |
 | Jennifer Hill | Sunday, August 26, 2012 Lifetime Chicago Triathlon | (triathlon) | 3:17:00 | (finish place not available) | 101.3% |