The Welsh outfit were barely surviving in the lower divisions while Leicester were enjoying a six-year run in the Premier League at the end of the 20th century.
The Swans have since gone on a remarkable journey which saw them almost bypass a Leicester side slipping alarmingly in the other direction on their way to consolidating themselves in the big time.
They have faced each other only four times in the league - the Championship - and once in the FA Cup, during the past 28 years, with the Midlanders having won on three occasions to Swansea's two.
Both are in need of victory this weekend as they try to regain some of the early-season momentum lost by neither of them having tasted success during October, with Swansea winless in five matches in total.
Three straight wins from the start of the season seem a long time ago now for Swans boss Garry Monk, whose frustration boiled over in the aftermath of their 2-1 defeat to Stoke City at the Britannia Stadium.
The 35-year-old faces an FA charge after describing referee Michael Olivier's award of a first-half penalty to the Potters as a "disgusting decision", moments after accusing Victor Moses of 'cheating' to win the spot kick.
Wilfried Bony had previously scored from the spot for Swansea and will continue up front this weekend, despite having not yet matched the form of last season which saw him net 16 Premier League goals.
Monk is not likely to rush into changes elsewhere either as he attempts to rediscover a winning formula, although Jonjo Shelvey should return in place of Tom Carroll in midfield after serving a suspension.
Winger Riyad Mahrez may return after sitting out the 1-0 defeat to Newcastle United, while Jamie Vardy is also in contention for a recall to a forward line that will be spearheaded by five-goal striker Leonardo Ulloa.
Swansea are eighth in the table with 11 points from eight games, with Leicester seven places below them.
Possible starting lineups
Swansea: Fabianski; Rangel, Fernandez, Williams, Taylor; Shelvey, Ki; Dyer, Sigurdsson, Routledge; Bony
Leicester: Schmeichel, De Laet, Morgan, Moore, Konchesky; Cambiasso, Hammond, Drinkwater; Mahrez, Vardy, Ulloa
Sports Mole says: 2-1