In late July 2001, Martin O’Neill swooped to sign Leicester City’s left winger, Steve Guppy for a modest fee of £750,000. O’Neill was well aware of Guppy’s capabilities as he had purchased Guppy for Leicester back in 1993 when he was manager of the (then) Filbert Street club.

The day Guppy signed was a most hectic one for Martin O’Neill and Celtic. O’Neill presided over three incoming transfers on one day, with John Hartson’s £6M move from Coventry being the obvious one to attract the greatest publicity. Hartson was then joined at Celtic Park by Steve Guppy and Momo Sylla, a £650,000 purchase from St Johnstone. Later that evening O’Neill led his team to Old Trafford where Celtic defeated Alex Ferguson’s, Manchester United, 4-3 in a memorable game for Ryan Giggs’ testimonial match.

Guppy had enjoyed a productive period under O’Neill at Leicester. The Foxes enjoyed a successful spell with Guppy had the honour of representing England in a friendly against Belgium in 1999. He was an orthodox left winger and was seen as a valuable addition to Celtic’s squad with newspapers reporting that he had an assist rate in the Premiership comparable to David Beckham’s.

The Englishman arrived at a fascinating time in Celtic’s history. In his first full game he played in a Champions League qualifier against Ajax at Parkhead. Celtic held a 3-1 win from the first leg in Amsterdam and looked unsure whether to ‘twist or stick’ on the night. Ajax deservedly won 1-0 but couldn’t do any more and Celtic nervously won through to the Champions’ League group stages for the first time.

Steve had stiff competition for the wide left midfield berth from both Alan Thompson and Bobby Petta. Petta seemed perennially to be injured and Thompson had quickly become a fans favourite after a number of impressive performances. Steve found it hard to break in to the team on a regular basis until March 2002. He was a surprise choice to face Rangers at Ibrox and he performed well on a day when Celtic played well within themselves to get a 1-1 draw.

After that Steve was a regular in the league run in. The league title was clinched on a memorable,  bright sunny day at Parkhead when Livingston were demolished by 5-1. Steve had perhaps his best game for Celtic on this day and two of his precise crosses were converted by Henrik Larsson and John Hartson. Steve and the happy Celtic players celebrated with the supporters long after the final whistle.

There was disappointment for the English winger in August 2002 when he played in both legs of the Champions League qualifiers against FC Basle when Celtic were eliminated narrowly on the away goals rule. This disappointment was quickly lifted when the Celts embarked on their memorable ‘Road to Seville’ when they reached the UEFA cup final in Spain.

Guppy played a role against all the opposition up to, and including, the quarter finals against Liverpool. His best performance came in the away leg against Graeme Souness’ Blackburn Rovers in November when Celtic surprised many English observers by winning convincingly on English soil. Sadly for Steve, a hernia problem meant that he missed the semi finals against Boavista and the final against Porto.

At the beginning of the 2003-04 season Steve found himself edged out by youngsters, Shaun Maloney and Liam Miller, as places in the team became keenly contested. Steve played only sporadically in cup ties and in January 2004 he decided to move back to Leicester City to play regular football.

Steve Guppy had a hard time winning over an element of the Celtic support, who preferred Alan Thompson’s more combative style on Celtic’s left flank. He was a more orthodox winger who concentrated on getting cross balls over for the Celtic strikers to attack. At this time Celtic had three of the best headers of a ball in European football in Henrik Larsson, Chris Sutton, and John Hartson. Each one of these players benefitted from Steve Guppy and they can testify to the quality of service he supplied from Celtic’s left wing during his time at Celtic Park.