Shillingford was a stylish and determined middle-order batsman who made his international debut at age 32 against Pakistan in March, 1977, where he played alongside Sir Clive Lloyd, Sir Viv Richards, Sir Gordon Greenidge and Sir Andy Roberts. In his second Test he made a huge impact with a memorable topscore of 120 at the Bourda Ground in Guyana. Overall, he played four Test matches and two One-Day Internationals.

After his career ended, Shillingford held several roles in regional cricket including manager and coach of the West Indies Under-19 team, selector and coach of the Windward Islands team, and made a major contribution to the development of the game at all levels in his native Dominica. A stand at the Windsor Park Stadium is named in his honor.