 Cowlishaw had been manager of the Kickers since 2000, during which time he coached the team to a Central Conference title in his debut year, two USL2 regular season titles in 2006 and 2007, three US Open Cup quarter final berths in 2001, 2004 and 2007, and two USL Second division championships, in 2006 and 2009.He is a two-time USL2 Coach of the Year nominee, helped guide the organisation to four USL Organization of the Year awards (1995, 2000, 2006 and 2007), the Fair Play Award in 2004, and was named FieldTurf USL2 Coach of the Year in 2006.On June 26, 2018, Cowlishaw stepped down as the head coach of the Kickers to assume the Director of Soccer role with the club.