Jupp began his career as a trainee with Fulham where he made more than 100 appearances before he moved to Wimbledon for £200,000. He later had spells with Notts County and Luton Town before joining Southend United, where he helped the club to two consecutive promotions - including scoring the decisive goal in the Football League Two Playoff final in 2005 against Lincoln City;[3] his only goal for the club.
He signed for Gillingham on 22 May 2006 and made his debut in the 2–1 home win over Huddersfield Town on 5 August. He left the club by mutual consent on 17 December 2007.[4] He joined Bognor Regis Town in January 2008.[5]
Jupp, who also worked as a football coach at Dorset House School in nearby Pulborough, announced his retirement from football in July 2009. However, in September 2010, he made a comeback and returned to Bognor.[6]
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