Chelsea's relationship with the European Super Cup comes full circle on Friday when the winners of the first final at the picturesque Stade Louis II face Atletico Madrid in the last one to be staged there.
Chelsea, at the time holders of the Cup Winners' Cup, beat European champions Real Madrid 1-0 in 1998 and now, as European champions themselves, they are back to face Atletico, the winners of last season's Europa League.
Chelsea's win 14 years ago, secured by a late Gus Poyet goal over a Real side that included Raul, Roberto Carlos, Clarence Seedorf and Fernando Morientes, began a trend.
Of the 14 finals played in Monaco in the traditional curtain-raiser to the European club season, the European champions have lost eight times to the Cup Winners' Cup holders and then subsequently the UEFA Cup and Europa League winners.
Atletico, like Chelsea, have also beaten the European champions in Monaco, scoring a 2-0 victory over Inter Milan at the Stade Louis in 2010.
However, unlike in 1998, Chelsea will start as favourites after a fine start to the domestic season in which they have won their opening three Premier League matches.
"Of course we want to extend that run with another win on Friday," coach Roberto Di Matteo, who played in Chelsea's 1998 win over Real, said after the victory over Newcastle United on Saturday. "And you can never win enough trophies."
Chelsea defied the odds last season to realise the dream of billionaire Russian owner Roman Abramovich and win the European Cup on penalties against Bayern in Munich.
Abramovich is a regular visitor to Monaco with one or more of his yachts regularly berthed in the harbour beneath the famous casino, and he has gambled some 80.0 million pounds on new players since the night Chelsea reached the European pinnacle at the Allianz Arena.
Brazilian playmaker Oscar, Belgian midfielder Eden Hazard, Spanish defender Cesar Azpilicueta, Germany's Marko Marin and Nigerian-born Victor Moses have arrived at Stamford Bridge while Salomon Kalou and Didier Drogba are among those who have left.
There is no doubt Abramovich would like to sail away from Monaco with another trophy in the locker before the Super Cup begins its travels around Europe. Following a suggestion by UEFA president Michel Platini to rotate, next year's match will be in Prague, the 2014 final in Cardiff and the 2015 game in Tbilisi.
Like Di Matteo, Atletico's charismatic Argentine coach Diego Simeone has just begun his first full season in charge at the Vicente Calderon and still has most of the players in his squad who helped win the Europa League.
They appear to have fended off interest from wealthier rivals in striker Radamel Falcao, the Colombia international known as "the tiger" who netted 24 goals in La Liga last season and 12 in Europe.
Falcao has picked up where he left off and scored a fine hat-trick in Monday's 4-0 mauling of Athletic Bilbao, the team they beat 3-0 in the 2012 Europa League final.
He took his tally against the Basque club to seven in three matches, having also scored twice in a 2-1 success in La Liga last March.
"This gives us a lot of encouragement to face the game on Friday," Falcao told Spanish television after the Bilbao match. "We knew that if we won this game we would have more confidence to face Chelsea."
The game will also be an interesting one for 20-year-old Belgian keeper Thibault Courtois, who is on loan for a second season at Atletico from parent club Chelsea.
"Its special for me as the game is against my club, But I play for Atletico: it's me against Chelsea and I want to win it," he told UEFA.
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