I’ve only played a handful of games in the Premiership I'm hardly a star!" 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. He played in the 1996 Anglo-Italian Cup Final, as Vale lost 5–2 to Genoa. In nearly three seasons at the then First Division club he became a firm fan favourite and is now classed a club legend after his memorable performances on the left wing. 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. He was cup-tied for their victory in the 1997 Football League Cup Final. It was in his first spell with the Foxes that he was most successful, playing in over 140 matches under O'Neill. He gained League Cup honours with Leicester City in 2000, having also reached the final in the previous season. In August 2001, Guppy re-joined O'Neill at Celtic for £700,000, where he spent two-and-a-half years. During his time at Celtic, they won the Scottish Premier League in his first season at the club. The following season, 2002–03, Guppy had a number of injury problems, meaning he missed the 2003 UEFA Cup Final. In 2003-04 Guppy only made one appearance for Celtic, in a Scottish League Cup tie against Partick Thistle, before leaving Celtic to re-join Leicester City in January 2004. Guppy left Leicester in the summer of 2004, to try to get to the US to play. He then spent a brief spell at Leeds United in August 2004, scoring once against Nottingham Forest, before gaining a short-term deal at Stoke City followed by a short spell back at Wycombe, scoring once against Swansea City. He moved to the United States but his short stint in Major League Soccer with Washington-based D.C. United was ended prematurely due to injury, and he was released by the club after playing in just five league games in which he was featured in a starting line-up alongside Freddy Adu in midfield. In August 2006 he signed for Stevenage Borough, scoring his first goal for them in a 1–1 draw at Exeter City. With Jeff Kenna, Guppy became the first player to play at both the new Wembley and the old Wembley. This was achieved on 12 May