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5 biggest round-of-16 upsets in UEFA Champions League history

Robin Bairner
Top 5 / Top 10
22.39K   //    06 Mar 2018, 17:20 IST

Real Madrid v Club Atletico de Madrid - UEFA Champions League Final
Will we see one this knockout stage?

Over the course of the next eight days, Europe’s top 16 teams will be whittled down to only eight as the quarter-finalists of the Champions League are decided.

The Champions League’s expansion in 2003-04 doubled the number of teams in the competition and thereby doubled the number of teams who reached the knockout phase. As a result, that was the first time since the reinvention of the competition that there was a classic round of 16.

Just as the big guns typically find their way through the group stage unharmed, they also tend to come through the first elimination round without too many issues, though over the years there have been instances of giant-killing.

Manchester City, Liverpool and Bayern Munich already have one foot in the final eight, given the emphatic nature of their first-leg victories, but five places are up for grabs.

Shocks at this stage of the season are not commonplace and the potential for any genuine upsets this year is slim. Shakhtar Donetsk have a strong chance of upsetting Roma, while Sevilla and Chelsea are very much in their ties against Manchester United and Barcelona respectively.

Here are five of the greatest upsets at this juncture of the competition.

#5 FC Porto v Manchester United (2003-04)

Manchester United v FC Porto
Manchester United v FC Porto

Jose Mourinho’s Porto might have been UEFA Cup holders when they were pitted against Manchester United but they were not given much of a chance against far more seasoned European opponents, who contained the likes of Ryan Giggs, Paul Scholes and Roy Keane.

Certainly, in the early minutes of the first leg, it looked like a routine success for United. Scholes might have seen his free kick stopped, but Quinton Fortune fired home the rebound. Sir Alex Ferguson’s side had not conceded in five European matches but Benni McCarthy scored twice to turn the tie on its head.


In the return leg, United took a stranglehold of the tie in the opening half as they got the better of a war of attrition that would become a Mourinho trademark in the years to come. Paul Scholes put the home side ahead of away goals and on the stroke of half-time had a goal fatefully and wrongly disallowed for offside.

United chased a second goal, throwing on Cristiano Ronaldo for defensive midfielder Darren Fletcher, but in the last minute, Tim Howard fumbled a routine free kick, which allowed Francisco Costinha to pounce.

Mourinho, whose side went on to win the competition by beating Monaco in the final, famously celebrated by sprinting down the touchline, and his rivalry with Ferguson had begun.

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Robin Bairner
UK-based freelance football journalist for the last decade, I've appeared in publications such as the Guardian, the Blizzard, When Saturday Comes, but can most frequently be found on I write about European football, and have worked at both World Cup 2014 and Euro 2016.
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