In addition to a successful nineteen-year club career, he earned England caps at under-21, semi-pro, 'B', and finally at full senior level.
Guppy was spotted playing for his local team, Colden Common and offered a chance with Southampton in March 1989.
He made a handful of appearances in the Saints reserves at the end of the 1988–89 season (but failed to break into the first-team)[4] before moving to Jim Kelman's Wycombe Wanderers in September 1989.
He was a virtual ever-present in Wycombe's debut 1993–94 season in the Football League, at the end of which they secured promotion to Second Division via the play-offs.
"[9] Vale was a step down, but another top manager – in the form of John Rudge, helped him focus on being a first-team performer again.
[6] Two days after signing for the club, on 26 November, Guppy made his debut in a 2–1 win over Millwall, where he collected assists for both goals.
In February 1997, he was tracked down by his former boss Martin O'Neill, who paid £850,000 to take him to Premier League club Leicester City for the first time.
[20] He then spent a brief spell at Leeds United in August 2004,[21] scoring once against Nottingham Forest,[22] before gaining a short-term deal at Stoke City, where former Vale manager John Rudge was director of football.
The club released him after playing in just five league games, during which he was featured in a starting line-up alongside Freddy Adu in midfield.
Borough won 3–2 despite being 2–0 down at half-time; Craig Dobson, who replaced Guppy on 63 minutes, scored the equalizing goal.
Guppy's first goal for the Rhinos came off of a header on 26 September in the final 10 minutes of the first round, first-leg play-off tie against the Charleston Battery.
[33] After a season as a player-coach at Rochester, Guppy was recruited for the position of assistant coach to Gary Smith at Major League Soccer team Colorado Rapids.
[36] In April 2013, Guppy followed O'Neill out of Sunderland as incoming manager Paolo Di Canio appointed his own coaching staff.
[39] O'Neill was sacked by Ireland in November 2018 following relegation out of the UEFA Nations League B Group 3, and Guppy also lost his position.