City's second season back in the Premier League, following promotion in 1996, included a difficult festive spell for Martin O'Neill's men, who went seven games without a win.
It was hardly the kind of form to give them confidence going into a clash with Sir Alex Ferguson's Manchester United at Old Trafford on Saturday 31 January, 1998.
You had to go back to April 1966 for Leicester's last win at Old Trafford, when a double from Mike Stringfellow secured a 2-1 win over a side including Bobby Charlton and George Best.
However, under O'Neill's management, City had earned a reputation as a side who could achieve anything on their day and so it proved to be the case on the final day of January.
United were reigning champions and fielded a starting XI featuring the likes of David Beckham, Ryan Giggs, Paul Scholes, Andy Cole and Ole Gunnar Solskjær.
However, after 30 minutes in Manchester, City were ahead, sparking jubilant scenes in the away end, as Tony Cottee pounced to inject new life into Leicester's 1997/98 campaign.
The Foxes would go on to enjoy victories over Leeds United and Chelsea in the weeks which followed, before sealing a 10th-placed finish in the Premier League.
Sixteen years later, Leicester, under the management of Nigel Pearson, were on a roll in the Championship and they mounted a bid to end a 10-year exile from the top flight.
On Tuesday 28 January, 2014, they travelled to St. Andrew's to face Birmingham City and to try and register an incredible eighth-successive league win.
The Foxes led half-way through the first half as David Nugent played in winger Lloyd Dyer, who powered the ball past Darren Randolph and into the roof of the net.
Meanwhile, Jamie Vardy, signed from Fleetwood Town in 2012, added a brilliant second goal late on, beat two defenders to fire home and secure a Club record successive victory.
While Peter Løvenkrands did get one back for Birmingham, there was no dampening the mood among Pearson's squad, who continued their run with another win at AFC Bournemouth.
City would only lose one more game all season, to Brighton & Hove Albion once promotion had already been secured, as the Foxes won the league with a staggering 102 points.
In the end, the 2013/14 season acted merely as the first act in a sensational era for the Club, which culminated with them lifting the Premier League trophy in 2016.
One of the defining nights of that season came on Tuesday 2 February, 2016 as Jürgen Klopp's Liverpool visited Filbert Way on a massive night for Leicester.
Claudio Ranieri's Foxes were top of the Premier League, despite pre-season title odds of 5,000/1, but their clash with Liverpool was the first of three important fixtures.
After tackling the Reds, City were due to travel to both Manchester City and Arsenal, but first they had to secure a positive result against their Merseyside visitors.
Despite many predicting Leicester would finally falter, the Foxes continued their excellent form into February, with Vardy netting a brace to seal a 2-0 success.
His first, meanwhile, remains one of the most iconic goals in King Power Stadium's history, as City's No.9 belted a magnificent volley over Simon Mignolet.
Ranieri's men also won at Manchester City, before a late loss at Arsenal, but they recovered to win the title by a margin of 10 points.