Although naturally a tricky winger, Guppy was occasionally deployed as a left wing-back during his time with the Foxes, including on his debut, as he became an integral part of the Club's success during the late 1990s.
Signed from First Division outfit Port Vale in February 1997, Guppy went on to make 189 appearances for Leicester across two spells, scoring 10 goals – and his initial transfer fee, a little under £1M, proved to be money well spent.
Brought to the Club by Martin O'Neill, the pair were already well acquainted, with Guppy having played under the Northern Irishman at Wycombe Wanderers, who enjoyed a remarkable rise from non-league to the second tier.
He had played over 200 times for the Chairboys at the beginning of the decade, before a short stint at Newcastle United in 1994.
Following his four years at City, he linked up with O'Neill once more at Celtic, enjoying two-and-a-half years in Glasgow before returning to Leicester for half a season in 2004.
His career then took him from Leeds United to DC United, via Stoke City and another stint at Wycombe, eventually retiring in America in 2008.
But it was at Filbert Street where he arguably made his biggest impact, playing Premier League football and making his senior England debut in 1999.
From his Premier League bow on 1 March, 1997, a 3-1 victory over Wimbledon at Selhurst Park, Guppy was known for his wicked delivery from wide areas, and the occasional goal.
Once the injury crisis which had positioned him as a wing-back abated, it was where he stayed for the majority of his Foxes career, adapting to his newfound role with much success and solidifying himself as a permanent fixture in O'Neill's side.
Two months after his arrival, Leicester won the League Cup for the second time in their history, beating Middlesbrough 1-0 in a replayed final at Hillsborough to secure the Club's first domestic cup triumph in 33 years.
Although cup-tied for that particular adventure, it gave Guppy the opportunity to play in Europe, for the first time, during the following season.
Along with Matt Elliott, also newly signed, from Oxford United, he featured in both UEFA Cup ties against Atlético Madrid in 1997 and would also play against Red Star Belgrade three years later - a feat only enjoyed by three other players: Elliott, Neil Lennon and Muzzy Izzet.
In Madrid, the visitors led via Ian Marshall's shock early goal but they were pegged back by Juninho. Christian Vieri then converted a penalty, given against Guppy in controversial circumstances, to hand Atlético a 2-1 lead.
During the return leg at Filbert Street, Leicester were denied several penalty claims of their own and Garry Parker was sent off in peculiar circumstances, before two second-half goals, including another from Juninho, sealed the Spanish side's place in the next round.
The 1997/98 league season, meanwhile, was equally as prosperous as the last and, following the ninth-placed finish the previous campaign, O'Neill's men backed it up by finishing 10th.
Guppy netted his maiden Leicester City goal during this, his first full campaign at the Club, scoring during a 3-0 win at home against Tottenham Hotspur in September 1997 and would also add his name to the scoresheet against Sheffield Wednesday in a 1-1 draw.
In 1998/99, meanwhile, Guppy produced his best goalscoring return of five goals, contributing to another top-half finish in the Premier League.
The winger played every minute of every league game that season – a run he continued into the following campaign – which, at the time, was a unique Premier League record.
He would soon receive international recognition for his marauding displays up and down the left flank. Following several England 'B' and Under-21s appearances, Kevin Keegan gave Guppy his only senior England cap. It came against Belgium in October 1999.
Back in the top flight, Leicester achieved their then best-ever Premier League finish of eighth at the end of 1999/00, and after the heartbreak of losing to Tottenham in the 1999 League Cup Final, went one better by returning to Wembley and defeating Tranmere Rovers in the 2000 edition.
Elliott was the hero that day, scoring twice, another player plucked from the Football League to help O'Neill achieve cup glory. Guppy, meanwhile, assisted both goals under the Twin Towers, further etching his name into Leicester City folklore.
Guppy started both finals and would also feature in another short-lived UEFA Cup journey in 2000/01, secured thanks to the cup win.
Now under the management of Peter Taylor, Leicester faced Red Star Belgrade, who got off to the perfect start in the first leg, scoring inside the first minute at Filbert Street.
The former Wycombe man played a big part in the equaliser, crossing for Gerry Taggart to head Leicester level on the cusp of half-time and that's how it finished, with the second leg being played in Vienna for security reasons.
With the support of a raucous, largely Red Star crowd, Belgrade took the lead once more and again City pegged them back before half-time, this time via Izzet's strike. But two second-half efforts proved to be the difference and knocked the Foxes out of Europe.
There was a certain symmetry to Guppy's Foxes career as he would score his first and final Foxes goal against Spurs, the latter during the last appearance of his first spell, a 4-2 Premier League victory on 5 May, 2001.
He made a further 15 top-flight appearances for the Club upon his return and finally signed off with a 3-1 win against Portsmouth on 8 May, 2004.
Given what he achieved, it is hard not to label Guppy as a Leicester City favourite who made a real impact on the Club and its supporters.