In 1889, Cassidy joined Bolton where he remained (with short spells with Carfin Shamrock and Celtic) for 9 seasons, making 219 appearances, scoring 101 goals.
In an FA Cup tie against Sheffield United on 1 February 1890, Cassidy scored 5 goals in a 13–0 rout, with a further 4 goals coming from Davie Weir.
Cassidy also scored Bolton's consolation goal in the 1894 FA Cup Final – Bolton were 4-0 down to Notts County when, with three minutes to play, County's goalkeeper George Toone came out to meet a Bolton attack only to slip while attempting to clear and leave Cassidy with one of the easiest cup final goals of all time.
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The 1894 FA Cup final was contested by Notts County and Bolton Wanderers at Goodison Park. Notts County won 4–1, with goals by James Logan (3) and Arthur Watson. Jim Cassidy scored for Bolton. Notts County became the first team, following the formation of the Football League in 1888, from outside the top flight to win the FA Cup.
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