Back after a two month long hiatus, everybody’s favourite continental cup competition returns this week. Resuming at the last 16 stage, the first knockout round has been the starting point for many a iconic Champions League triumph.
Introduced in the 2003/04 season, the last 16 round pits the winners and runners-up from the group-stage against each other, with some iconic ties having taken place over the years.
Here are five of the best last 16 ties involving English sides:
Manchester City vs Schalke 04 – 2018/19
Leading 2-1 with five minutes left in normal time, Schalke were on the verge of toppling Pep Guardiola’s Manchester City. However, a stunning free-kick from Schalke academy graduate Leroy Sane and a cheeky Raheem Sterling dink secured a first leg victory for the Blues.
Finely poised heading into the return leg at the Etihad Stadium, die Knappen were dreaming of recreating their 2010/11 heroics and making it to the semi-final. Prodigies like Manuel Neuer and Julian Draxler took the side from Gelsenkirchen to the brink of European glory in 2011. Instead, it was a massacre.
Seven goals from six different scorers gave City a 10-2 aggregate victory and the result remains the equal second highest knockout score in Champions League history.
Such was the embarrassment, Schalke manager Dominic Tedesco was relieved of his duties after the match. City’s joy was short-lived: they were dumped out of the tournament in dramatic fashion by Tottenham Hotspur in the next round.
Arsenal vs Real Madrid – 2005/06
It had never happened before and it has never happened since. Two giants of European football coming head-to-head for the first time. Pure, unfiltered Champions League joy.
At that time, nine-time winners Real Madrid had stumbled in the group-stage, finishing runners up to Ligue 1 outfit Olympique Lyonnais. By contrast, Arsene Wenger’s Arsenal had been imperious: five wins out of six, unbeaten and group winners. Their reward? A first-ever meeting with Los Blancos.
Wheeling away with stretched out arms, the entire Bernabéu hissed with disdain at the sight of Thierry Henry’s celebrations. After picking the ball up deep in the Real half, the Frenchman set off on a slaloming run, leaving behind the entire Madrid backline, before slotting calmly past Iker Casillas. Vintage Henry.
#TBT to when Thierry stunned Real Madrid on their own turf 🤩
🗓 #OnThisDay in 2006…
🏴 The first-ever English side to win at the Bernabeu pic.twitter.com/y10LxxhjUh
— Arsenal (@Arsenal) February 21, 2019
A stale, but crucially goalless affair in the return leg meant Arsenal had done it. A 0-0 draw at Highbury was enough and Real’s La Décima hopes had been shot down by the Gunners.
Wenger and Henry would have a Paris rendezvous with Barcelona come May, but the ten men of Arsenal would eventually succumb to La Blaugrana and today the prospect of a first ever Champions League victory for Arsenal seems further away than ever.
Manchester United vs Porto – 2003/04
Rushing down from the dugout stairs and sprinting towards the travelling fans, a fresh-faced Portuguese manager had stunned Old Trafford.
This was the first season where a last 16 stage was played, replacing the previously used second group-stage and it threw up some classics: Bayern Munich were thrown into a heavyweight clash against Real Madrid and plucky Deportivo de La Coruña toppled Italian giants Juventus. But it was the events unfolding between Manchester United and Porto that caught Europe’s imagination.
Heading into the second leg with a 2-1 aggregate lead, José Mourinho’s band of youthful starlets were travelling to Manchester to cause an upset. With the events of 1999 still fresh in the memory, the Old Trafford crowd were expectant: an away goal in hand, United were still well poised to progress to their tenth consecutive UCL quarter-final.
A United victory seemed an inevitability and it was set in motion on the half-hour mark – a glancing Paul Scholes header put the Reds ahead on the night and on aggregate. Scholes had bagged a double shortly before half-time, only to be denied by the only person in the stadium that thought the midfielder was in an offside position. Assistant referee’s flag raised, no goal.
The reigning Premier League champions continued to probe in the second half, but the Porto defence stood tall. Not even the talents of a pimple-covered Portuguese teenager in Cristiano Ronaldo could find a breakthrough and the Dragões entered added time needing just a goal to progress. Mourinho time.
Parrying a Benni McCarthy freekick into the path of Costinha, Tim Howard quickly became the loneliest man inside Old Trafford. United were out. English football’s first taste of the ‘special one’, Alex Ferguson’s men had been trumped.
The Porto legend continued all the way to the final, where they cruised past Monaco and lifted their second European Cup. Mourinho was back in England twelve months later, tormenting Ferguson and the Premier League with his rampant Chelsea side, whilst Porto have failed to get past the Champions League quarter-finals ever since.
Liverpool vs Bayern Munich – 2018/19
We’re used to hearing commentators wax lyrical about the glorious ‘Anfield lights’ whenever Liverpool play in the Champions League, but the then five times winners of the competition’s best last 16 triumph came away from home.
If the 0-0 in the first leg was enough to bring about an existential questioning of all the reasons you put yourself through the pain of watching football, the second leg in Bavaria put the beauty back into the game.
Jurgen Klopp had suffered defeat against Bayern Munich more times as a manager than any other club and after a stumbling group-stage performance Liverpool were matched against the record Bundesliga champions in the competition for the first time since 1981.
Bayern Munich have come a long way in a year…
They simply couldn’t deal with Liverpool and Sadio Mane last season 👀pic.twitter.com/PYn9C5o8Uh
— Goal (@goal) August 24, 2020
Nullifying an attack of Robert Lewandoski, James Rodriguez and Kingsley Coman in their home leg, the previous season’s finalists travelled to Munich knowing a goal without reply at the Allianz Arena would send them through. In the end, they got three, comfortably dispatching of Bayern and progressing to the quarter-finals.
On a trademark European night, goals from Saido Mane and Virgil van Dijk set the tone for the rest of the competition, which would eventually end with Liverpool lifting the coveted ‘number six’ on a starlight night in Madrid. Klopp finally had his red-ribboned trophy and a victory over eternal rivals Bayern on the way made it that little bit sweeter.
Chelsea vs Barcelona – 2004/05
Chelsea coming up against Barcelona has felt more like a domestic fixture, such is the regularity the two have faced each other in recent years: since the turn of the millennium, the pair have played each other 14 times in the Champions League.
After getting a taste for the competition the season prior, Mourinho was appointed as Chelsea boss by billionaire Russian oligarch, Roman Abramovich to bring European glory to West London. Sitting comfortably at the top of the Premier League table and having already bagged his first trophy in English football the week before, the ‘special one’ was tasked with overturning a first leg deficit against the La Liga leviathan.
Barcelona travelled to Stamford Bridge with a slender 2-1 aggregate lead, but after a twenty minute blitz, Frank Rijkaard’s men were 3-0 down on the night with an almost impossible task ahead.
Starved for ideas, the Catalans relied on the brilliance of Ronaldinho to resurrect their chances in the tie. The Brazilian’s second of two, a sublime strike in which the two time World Player of the Year shimmied before poking the ball through a crowd of defenders and past a bemused Petr Čech, put Barca ahead via the virtue of away goals.
If the Ronaldinho goal was made on the samba soaked sands of the Copacabana beach, the Chelsea winner was straight off the mud baths of the Hackney marshes. A whipped ball from a corner was met by the forehead of John Terry. A captain’s goal.
Mourinho’s latest Champions League coup d’etat against European royalty had sent the Blues to a quarter-final in the competition for only the third time.
Tragedy was to strike for Chelsea in their semi-final clash in Merseyside; Luis García’s ‘ghost goal’ set up a date with AC Milan in Istanbul for Liverpool, whilst Abramovich would have to wait seven long years before bringing the Champions League trophy to the Bridge.