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Kirkwood was one of the directors in charge of training players for the F.A. Cup in 1905 when Everton got to the semi-final. Kirkwood signed some great Evertonians. On 8th May 1905 he took on Harry E. Cooke who worked for Everton as a player and trainer for half a century. On 23rd April 1907 he travelled to Scotland to sign J.S. Maconnachie who made 270 starts for Everton from 1907-20.