1. Milan vs Inter, 2002/03 (Champions League semi-final)
The Derby della Madonnina is not what it used to be. Milan and Inter have shown signs this season that they are belatedly beginning to shake off their respective malaises, but it could be a long while yet before we see the clubs from Italy’s second city competing in the last four of the Champions League again.
The last time they both got there in the same campaign was in 2002/03, when Carlo Ancelotti and Hector Cuper’s sides were drawn against one another in the semi-finals.
A Milan team containing Paolo Maldini, Andriy Shevchenko, Andrea Pirlo and Alessandro Nesta squeezed past the Inter of Javier Zanetti, Fabio Cannavaro, Hernan Crespo and Alvaro Recoba on ‘away’ goals, with UEFA rules deeming the Rossoneri’s strike at San Siro to be worth more than their joint tenants’ at the same venue.
2. Real Madrid vs Atletico Madrid, 1958/59 (European Cup semi-final)
Atletico Madrid were just seconds away from winning the Champions League against their city rivals in 2014, only for Sergio Ramos to equalise deep into stoppage time and los Blancos to run away with it in the extra 30 minutes. That encounter came a full 55 years after the duo’s European Cup semi-final in the late 1950s, though, a two-legged tie that required an additional 90-minute play-off to separate the sides.
Atletico were taking part in the competition despite finishing as runners-up in the previous La Liga campaign – Madrid qualified as holders, so Spain’s place was filled by their neighbours. The Rojiblancos were defeated 2-1 in the first leg despite taking the lead through Chuzo in front of a 120,000-strong Bernabeu crowd. A 1-0 win in the second clash forced a third, in which goals from club legends Alfredo Di Stefano and Ferenc Puskas booked Madrid’s place in the final for a fourth successive season.
3. Spartak Moscow vs Dynamo Kiev, 1994/95 (Champions League group stage)
The most successful teams in Soviet Top League history renewed acquaintances in the Champions League three years after the dissolution of the federation.
Over 90,000 supporters flocked to Respublykanskyi Stadion to witness Dynamo defeat their old rivals 3-2 in the first round of Group B matches, with Spartak surrendering a 2-0 lead in the second half; those were the only points the Ukrainians collected, however, with Spartak getting their revenge with a 1-0 win in Moscow two months later.
Despite achieving creditable draws against Bayern Munich and Paris Saint-Germain, the Russians crashed out alongside Dynamo, who were thrown out of the following year’s edition of the competition for attempting to bribe the referee ahead of a group game with Panathinaikos.
4. Juventus vs Fiorentina, 1989/90 (UEFA Cup final)
Supporters of other Italian clubs tend not to like Juventus, a feeling that’s particularly strong among followers of Fiorentina, who to this day remain convinced that their team was cheated out of the 1982 Scudetto that ended up in the Bianconeri’s trophy cabinet.
The bad feeling intensified in 1990 when star man Roberto Baggio was sold to the Turin-based giants for £8 million, a move that led to riots in the streets of Florence.
The UEFA Cup final took place in the midst of such an environment, with Fiorentina desperate to get one over on their sworn enemies. Rumours of Baggio’s impending transfer began to surface just before the first game – which Juve won 3-1 – with the deal completed shortly after the Divine Ponytail failed to inspire a comeback in a goalless second leg.
5. Hamburg vs Werder Bremen, 2008/09 (UEFA Cup semi-final)
Werder Bremen defeated rivals Hamburg on penalties in the German Cup a week before going down 1-0 in the first leg of their UEFA Cup semi-final at Weserstadion, but strikes from Diego, Claudio Pizarro and Frank Baumann saw Thomas Schaaf’s charges advance on away goals after triumphing 3-2 in the return game.
With thousands of Hamburg fans behind them, Shakhtar Donetsk narrowly defeated the four-time German champions 2-1 in the final.
6. Barcelona vs Real Madrid, 2010/11 (Champions League semi-final)
In terms of pre-match mind games, there was only one winner. “In this room, he is the chief, the f***ing boss,” raged Pep Guardiola after Jose Mourinho successfully got under the Catalan’s skin by suggesting he was rather fond of criticising referees.
Perhaps, though, verbal jousting in the press room is not as significant as is often assumed: on the pitch, Guardiola’s Barça secured a 3-1 aggregate victory to set up a final with Manchester United at Wembley.
Madrid managed a respectable result in the second leg at the Camp Nou, but by then the damage had already been done. Six days previously, Barcelona turned in a terrific performance at the home of their greatest rivals, winning 2-0 thanks to a brace from Lionel Messi, whose second effort – when he dribbled around half of the Madrid team before sliding the ball past Iker Casillas and into the net – remains among the best he has ever scored.
In total, El Clasico has hoisted itself onto the European stage four times, with the pair also meeting in 1960, 1961 and 2002.
7. Rapid Bucharest vs Steaua Bucharest, 2005/06 (UEFA Cup quarter-finals)
The 2005/06 UEFA Cup received a great deal of interest in Bucharest, with Dinamo, Rapid and Steaua all qualifying for the group stage.
While Dinamo finished bottom of their section after taking only four points from the 16 on offer, the latter duo advanced to the quarter-finals, where they were pitted against each other in continental competition for the first time.
A 1-1 draw in the first leg saw Steaua secure the away goal that would prove pivotal, with a 0-0 stalemate a week later knocking Rapid out and sending Cosmin Olaroiu’s men through to the final four.
8. Sevilla vs Real Betis, 2013/14 (Europa League last 16)
There can’t be a worse way to lose a game of football than this.
Real Betis took a 2-0 lead into the home leg of their Europa League last-16 tie with their bitter rivals in 2014 – Salva Sevilla grabbed the second, just to rub salt into wounds – and looked like going through despite Sevilla pulling a single goal back with the final 15 minutes approaching.
Carlos Bacca levelled the scores to force extra-time, though, with Sevilla going on to win the penalty shootout thanks to Alberto Moreno and Ivan Rakitic keeping their cool, and Betis’s Alfred N’Diaye and Nono losing theirs.
Liverpool and Manchester United fans will want to avoid such a gut-wrenching fate at all costs.
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