Chelsea will travel to Northern Ireland in the coming days for its UEFA Super Cup match against Villarreal. Opportunities to kick the season off by winning a European Cup are rare, but the Blues have spurned such chances far too many times in the bygone decade. This is one trophy that has evaded the team in times of the Roman Empire. In fact, Chelsea’s last—and only—win in the Super Cup came five years before Roman Abramovich bought the club from Ken Bates. Those were different times and that was a different team.
In this piece, we recap the Blues’ rare achievement and the subsequent failures of their successors. This is Chelsea’s history in the UEFA Super Cup:
Chelsea 1-0 Real Madrid (1998)
23 years ago, Chelsea went to Monaco and beat Champions League winners, Real Madrid, to lift its first—and only—UEFA Super Cup. Those were different times, the pre-Roman era of hipster signings, title challenges and identity crises. An era, which, in the Chelsea lore, has been restricted in its purpose as a retort to be used against ignorant rival fans. Was Chelsea even relevant before 2004? Yes, and we won more European Cups than you, ha!
On May 13, 1998, Chelsea won the UEFA Cup Winners’ Cup by beating Germany’s VfB Stuttgart 1-0 in the final. A week later, Real Madrid overcame Juventus by the same scoreline to lift the Champions League, and in doing so, set up the Super Cup clash against the Blues. The two teams traveled to Monaco three months later to play in the final, after UEFA decided to replace the two-legged tie with a one-off game.
Marcel Desailly and Frank Leboeuf was the starting centerback partnership for Chelsea that night while Gianfranco Zola, Roberto Di Matteo and Pierluigi Casiraghi were deployed up front from the start. Dennis Wise captained the team, and future Chelsea coaches Eddie Newton and Jody Morris found themselves sitting beside their then-manager Gianluca Vialli on the bench.
Real Madrid—with the likes of Raul, Fernando Hierro, Roberto Carlos, Clarence Seedorf, and others—was the favorite heading into the match, but the Blues gave them and their manager Guus Hiddink a tough time throughout. It took 83 minutes for Vialli’s side to find the breakthrough, though, and it was substitute Gus Poyet with a stunning strike from outside of the box that sealed the win for the Blues.
Chelsea 1-4 Atletico Madrid (2012)
There have been plenty of excellent individual performances against Chelsea over the years, but none were more frightening than Radamel Falcao’s in the 2012 UEFA Super Cup for Atletico Madrid. The Colombian shred the Blues’ defense to pieces and firmly established himself as one of the finest strikers of his generation before injuries and bad loans would derail his career. It was a display which—safe to say—haunts the Chelsea faithful to this day, and in retrospect, might have pushed the club toward sanctioning a miscalculated loan move for the forward some years later.
By winning its first Champions League trophy in 2012, Chelsea set up the Super Cup clash against Atletico Madrid, who had won the UEFA Europa League earlier that year. Club legend Didier Drogba had left the club earlier that summer, but the Blues hoped one of their new signings would be heir to the king. One of those new signings—a certain Eden Hazard—started the match while another, Oscar, came off the bench. Both their efforts would be in vain that night though.
Falcao tormented David Luiz all night; he got the better of the Brazilian as early as the sixth minute and then took advantage of his slip-up in the 19th to put Diego Simeone’s side two goals up. The Colombian completed his hat-trick in the 45th minute of the match, putting the game to bed. Miranda put the Rojiblancos 4-0 up at the hour mark before Gary Cahill pulled one back to save the Blues from complete humiliation on the night.
Chelsea 2(4) – 2(5) Bayern Munich (2013)
Chelsea took on Bayern Munich in the 2013 UEFA Super Cup. The Blues were competing in the cup for the second consecutive year—having won the UEFA Europa League. Bayern, meanwhile, had overcome the disappointment of losing the Champions League final in its own backyard in 2012 by winning the trophy the subsequent year.
Bayern against Chelsea—the 2012 UCL final rematch—wasn’t the only narrative floating around Eden Arena in Prague. The match also resumed the rivalry between Jose Mourinho and Pep Guardiola, who often found themselves in the opposite dugouts for El Classico, but had since gone their separate ways.
Once Chelsea’s record signing, Fernando Torres gave the Blues the lead in just the eighth minute of the match, finishing emphatically past Manuel Neuer in goal. Franck Ribery scored the equalizer in the 47th minute, and thanks to a couple of excellent saves by Neuer, the game went into extra time.
Mourinho, however, was left a man short for the extra 30-minute period due to Ramires receiving his marching orders in the 85th minute. Nonetheless, his team did take the lead once again, thanks to a little bit of magic from the brilliant Hazard in the third minute of extra time. Sadly, Hazard’s effort was wasted when Bayern pulled level for the second time on the night through Javi Martinez, who diverted the ball past Petr Cech with almost the last kick of the game.
A penalty shootout ensued between the two teams for the second time in two years. This time, however, it was Bayern who came out on top after a young kid named Romelu Lukaku (wonder what became of him) saw his effort saved by the opposing goalkeeper.
Chelsea 2(4) – 2(5) Liverpool (2019)
Two goals in normal time, two in extra time, a narrow loss in the penalty shootout with a young striker missing the crucial kick—the Blues’ 2019 loss in the Super Cup bears freakish similarities to the one they suffered six years prior.
This time, the Blues faced domestic rivals, Liverpool, in Istanbul, a city with significant connotations for the Reds following their miraculous Champions League win back in 2005. The 2019 edition of the Super Cup was historic too, as it was the first time two teams from England faced off in the competition. Chelsea, the Europa League winners a season ago, faced against Liverpool, who had won the Champions League. Frank Lampard, who had lost the competition twice in 2012 and 2013, returned in the Blues corner as the head coach, along with an army of youngsters. It was the first big European night for the likes of Mason Mount, Fikayo Tomori and Tammy Abraham—all of whom played in the match.
Yet, it was veteran Olivier Giroud who gave Chelsea the lead in the 36th minute. However, Sadio Mane hit back just after the break to make the score 1-1 and push the tie into extra time. Mane scored again in the 95th minute, but a Jorginho special from the spot ensured that the tie would be decided by a round of penalties.
As was the case in 2013, Chelsea’s opponents scored all five of their spot-kicks. The Blues matches the Reds for the first four, but Abraham missed his chance from the spot to hand the cup to Liverpool.
What do you think the outcome will be this time around? Let us know in the comments or on Twitter!