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Born in Irvine, Wilson started his football career at local club Irvine Meadow before moving onto Clyde F.C. in Glasgow.
Two of Wilson's brothers were also professional footballers. David, capped once by Scotland, spent most of his career with Oldham Athletic, while James mainly played with St Mirren.1
He moved to Sheffield in 1900 where he spent the rest of his playing days. During his time at The Wednesday he won 2 League Championships and an FA Cup Winner's medal. He became the clubs all-time record top scorer with 216 goals and was top scorer in six different seasons. He appeared for the team 545 times, more than any other player. Both records stand to the present day. He also became the oldest player to play for the Owls before retiring on 10 March 1920 aged 39 years and 91. This record stood until it was beaten by Player/Manager Trevor Francis in 1993.