Pioneers
First winner: Bob Millar (1989)
First woman winner: Sherry Breshears (1991)
First to wear figure skates: Sandy Officer (1991)
First to wear goalie skates: James Burgess (1992)
First to portage a canoe: Scott & Bob Millar (1995)
First to carry the trophy through the entire race: Hugh Millar (1996)
First to complete the race while pregnant: Sarah Brandon (1998)
First person to wear shorts in the Carleton Cup: Scott Millar (1999)
Youngest person to participate in the Carleton Cup: Quinn Davidson, 2 months old (2000)
Oldest female to compete in and win the race: Eann Hodges, age 60 (2014)
First to complete the race in a wheelchair: Colleen McKane (2001)
First to be carried through the race in effigy [as a tribute!]: Adam Elliotson (2001)
First to complete the Cup in full hockey equipment: Calle Johannesson (2002)
First person to complete the race while impersonating Heino: Mark Hickox (2003)
First to wear a bikini top: Christine McCarthy (2003)
Youngest person to complete the Carleton Cup without assistance: Harvey Evers, 6 years old (2003)
First person to wear a Carleton Cup t-shirt while giving birth: Janis Davidson (2003)
First person to complete the race in full goalie equipment: Luis Freitas (2005)