 Tupling made his Hartlepool United debut on 26 December 1989 in a 4–1 home win against Scarborough.In the 1989–90 season he started 26 games and scored once, in a 2–1 home win against Rochdale on 10 March 1990.The following season he started 40 league games and scored twice, in the first game of the season in a 3–2 win away at Chesterfield and in the reverse fixture in January 1991, and helped the club gain promotion from the Fourth Division.