In May 1939, Phillip Hutton became a Director of Northampton Town Football Club, and the Playboy shoe was then advertised in the NTFC team sheets and programmes. In 1949 Hutton was instrumental in signing Arnold Woolard while holidaying in Bermuda. Playboy adverts continued to feature in the team programmes until the 1960-61 season when Phillip Hutton stepped down from his director’s role at the club.