Lillycrop was born in Gosport, Hampshire. He started his career playing for teams in the North Eastern League before transferring to Barnsley some time before 1910. He played in both FA Cup finals that Barnsley reached in 1910 and 1912. In the first, Barnsley lost in the replay to Newcastle. In 1912, Lillycrop played a critical role in the qualifying rounds, scoring 6 goals, several in replays. The 1912 Final went again to a replay but Barnsley won, defeating West Bromwich Albion by one goal in extra time. Given his key role in the qualifying rounds he does not feature much in the match day reports.