2007 when Kidderminster Harriers played Borough in the 2007 final of the FA Trophy at the new Wembley Stadium. Borough won 3–2 despite being 2–0 down at half time; Craig Dobson, who replaced Guppy on 63 minutes, scored the equalizing goal. Due to Stevenage winning, Guppy became the first ever person to win medals at both the old and new Wembley Stadium. In 2008, he headed for America again, signing with the Rochester Rhinos as Player and Assistant Coach. Guppy logged 1,520 minutes of playing time in 21 league matches, starting in most of his appearances. He tallied two assists, both of which came off of his trademark crosses from the left wing. 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. International career It was whilst at Leicester that he gained his only England cap, playing against Belgium on 10 October 1999. Manager Kevin Keegan described him as "a little bit like a left-sided David Beckham". Guppy remains the only footballer to have played for England under-21, England semi-pro, England B and the full England teams. Style of play Port Vale player and lifelong fan Tom Pope described Guppy as "a very tricky winger, one who could go on the inside or the outside", and a player with good crossing ability. In May 2019, he was voted into the "Ultimate Port Vale XI" by members of the OneValeFan'' supporter website. Coaching career After a season as player-coach at Rochester, Guppy was recruited for the position of assistant coach to Gary Smith at Major League Soccer team Colorado Rapids. Having had one more year on his coaching contract with the Rochester Rhinos, Rochester released Guppy from his duties, allowing him to move onto a higher level of coaching. He was assistant coach at the Colorado Rapids for three years, from 2009 to 2012. During his time at the club the Rapids lifted the MLS Cup in 2010. He left the club when the Rapids parted company with Gary Smith in November 2011. In March 2012, Guppy reunited with his old boss Martin O'Neill at Sunderland to work as a part-time coach, giving extra specialised sessions on technical work to "Black Cats" young players. A few months later he settled into the role on a full-time basis. In April 2013,