Wicklow, Ireland born outside left Jack Kirwan initially played Gaelic football for Dublin and won an All-Ireland medal with Dublin in 1894 when they defeated Cork by 1-2 to 0-5 after a replay. Although both the Final and the replay finished level, Dublin were awarded the Cup. He started his football career with Lancashire club Kirkdale in 1894 and then joined Southport Central of the Lancashire League where he attracted the attentions of both Everton and Blackburn Rovers. He opted to sign for Everton in July 1898 and was subsequently used to replace John Cameron who had been sold to Tottenham Hotspur. He made his Football League debut for Everton in a goalless draw at Preston North End in September 1898. During his only season with The Toffees he scored 5 goals in 26 appearances before following John Cameron to Tottenham Hotspur where the latter was now manager in the summer of 1899.
During his six seasons at Tottenham Kirwan scored 42 goals in 180 Southern League and FA Cup games for the club. He helped the Spurs win the Southern League in 1900 and the FA Cup in 1901, when they beat Sheffield United in a replay at Burnden Park after a 2-2 draw in the Final at The Crystal Palace, Tottenham thus becoming the only club outside the Football League to win the competition. In 1900 Kirwan also became the first Spurs player capped by Ireland when he played in a 2-0 defeat to Wales at The Oval, Llandudno. Between 1900 and 1909 Kirwan won 17 caps for Ireland, scoring twice and was a member of the Ireland team that clinched a share in the 1903 British Home Championship. His final game for Ireland was a 5-0 defeat to Scotland at Ibrox on 15th March 1909.
In May 1905 Kirwan left Tottenham Hotspur and joined newly elected Football League club Chelsea, playing in their inaugural League fixture at Stockport County. Over the next three seasons he made 76 appearances in total for Chelsea and scored 18 goals. In 1907 he helped Chelsea finish runners up in the Second Division and thus gain their first ever promotion. After leaving Chelsea he played a season for Clyde in 1908-09 before returning to the Southern League with Leyton in 1909, playing a further season for the East London club before retiring as a player.
With his playing days over, Kirwan moved to the Netherlands where he became Ajax’s first ever manager in September 1910. He led them to the Dutch top flight for the first time in 1911, returning to the UK in 1915 after the outbreak of the First World War. Kirwan later had a spell as coach of Livorno in Italy from 1923 to 1924.
Amongst his many caps and medals, one of Kirwan’s most prized possessions was the ball used in the 1901 FA Cup Final, and he kept it until he died in 1959, by when he was the last surviving member of the Tottenham team.