Rubuta ci gaba don wannan sakin layi - Lokacin da Longboat yaro ne, wani Mohawk () mazaunin wurin ajiyar, Bill Davis, wanda a 1901 ya zama na biyu a Marathon na Boston, ya ba shi sha'awar tsere. Ya fara tsere a 1905, ya gama na biyu a tseren ranar Victoria a Caledonia, Ontario. Babban nasararsa ta farko ita ce a cikin Around the Bay Road Race a Hamilton, Ontario a 1906, wanda ya ci nasara da minti uku. A cikin 1907 ya lashe Marathon na Boston a cikin rikodin lokaci na 2: 24:24 a kan tsohuwar hanyar 24-1/2 mil, minti huɗu da dakika 59 da sauri fiye da kowane daga cikin masu nasara goma na baya na taron. Ya rushe, duk da haka, a gasar Olympics ta 1908 marathon
, tare da wasu manyan masu gudu, kuma an shirya wasan kwaikwayo a wannan shekarar a Madison Square Garden a Birnin New York. Longboat ya lashe wannan tseren, ya zama mai sana'a, kuma a 1909 a wannan wurin ya lashe lambar yabo ta Professional Champion of the World ta hanyar kayar da Dorando Pietri da Alfred Shrubb a gaban taron jama'a.