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Kirkwood was part of the team which stormed to the top of Division 1 in the 1890-91 season. He made 19 league appearances that season, missing only 3 matches, and scored 1 goal. Yet, by the end of the season his career with Everton was under threat. On 23 March the directors decided not to re-engage him, but by 6 April they changed their minds and he was signed on the same wages as before.