Midway through the Club's maiden season back in the Premier League, Martin O'Neill's men headed into a League Cup Final against Middlesbrough on 6 April, 1997.
The Foxes had previously overcome Scarborough, York City, Manchester United, Ipswich Town and Wimbledon to reach the showpiece, but came up against a strong Boro outfit.
As well as future City manager Nigel Pearson at the back, the North East outfit also boasted the likes of Juninho Paulista, Emerson and Fabrizio Ravanelli among their ranks.
Indeed, it looked likely Boro would be triumphant after Ravanelli's opener four minutes into extra-time, but a last-gasp leveller from Emile Heskey booked a replay for Leicester.
Seven years later, meanwhile, the Foxes were bidding to make an instant return to the Premier League under the management of Micky Adams - and Nottingham Forest were the visitors on 8 April, 2003.
A four-game winning run led into the fixture for City, who had battled against administration and a transfer embargo for much of the 2002/03 season after moving to Filbert Way the summer before.
In front of a crowd of 32,065, a fraught affair unfolded, but a 37th-minute effort from youngster Tommy Wright was ultimately enough for Leicester to seal league win no. 25 that campaign.
City needed one more win for promotion, prompting Adams to say: "I don't want to rely on anyone else to do us any favours. No one has given us any help all season and I don't expect them to start now."
Another promotion campaign was on the cards in spring 11 years ago this weekend, on 11 April, 2009 to be precise, as Nigel Pearson's men travelled to Hereford in League 1.
A record-breaking season was reaching its climax but City had not - yet - got over the line and limited their stay in the third tier of English football to just one year.
They need not have been too concerned, though, as Matt Oakley, Lloyd Dyer and Steve Howard found the net at Edgar Street to register a comfortable 3-1 victory.
Pearson's Foxes were now on the cusp, ahead of the visit of Leeds United and a trip to Southend United, where they could wrap up the job, so long as they took a maximum of six points from both games.