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5 upsets in the Round of 16 in UCL history

UEFA Champions League has been home to Europe’s footballing powerhouse. Let us take a look at some of the ‘upsets’ the Champions league

Sourav Ghosh
Last updated: 09.03.2019
5 upsets in the Round of 16 in UCL history | Sports Social Blog

Everyone loves an upset in football, especially neutrals. There’s nothing like seeing a team punch above their weight and knock out the favorites of the tie. Over the years football has provided us countless upsets and Europe’s elite competition has been no exception. Yes, the UEFA Champions League has been home to Europe’s footballing powerhouses as well as minnows from smaller footballing nations. As expected, more often than not, the big teams have enjoyed quite some success but every year, we get our share of ‘upsets’. Be it in the group stages or knockout rounds.

While upsets in the group stages are rare, the knockouts have produced some absolute bonkers of games! Because over 180 mins, anything can happen and anyone can walk away with the game. That’s exactly why we love this competition so much.


With that in mind, let us take a look at some of the ‘upsets’ the Champions league has produced in the round of 16 stages.

1. Real Madrid - Ajax 2018/19 (Ajax won 5-3 on aggregate) -


Probably the game that prompted us to produce this list. If someone had told us what was going to happen at the Santiago Bernabeu even a few days ago, there were high chances we wouldn’t have believed them. Such was the nature of the fixture. Defending champions Real Madrid, despite their season struggles, were tipped to get past Ajax when the draw was made. They also proceeded in that fashion when they registered a 2-1 away victory. However, it was Sergio Ramos’ deliberate booking to get suspended in the next leg that backfired spectacularly. Come the game at Santiago Bernabeu, Ajax’s bright youngsters took the game to the home side. Goals from Hakim Ziyech and David Neres wiped out Real’s lead inside 18 mins. A peach of a goal from Tadic set the writing in stone as the capital side had to pull in 3 goals in the remaining time. Asensio got one but so did Schone and it was all over. A game that puts questions on Real Madrid and praises on Ajax. By far it has been the upset of the year, no arguments.

2. Arsenal - AS Monaco 2014/15 (Monaco won 3-3 on away goals) -


A case of too little too late for the Gunners as underdogs Monaco went gung-ho in the first leg at the Emirates. Kondogbia started the onslaught with a deflected effort off Mertesacker. Former Manchester United forward, Dimitar Berbatov doubled the lead. Chamberlain pulled one back for the hosts but the French side restored their 2 goal cushion via Yannick Carrasco. This meant Monaco had 3 away goals to rest on and that’s exactly what they did. Arsenal fell short of goals in the 2nd leg as their 2 goals scored by Ramsey and Giroud tied the score but they were eliminated on away goals rule.

3. AC Milan - Tottenham 2010/11 (Spurs won 1-0 on aggregate) -


Maybe a fixture most of us wouldn’t remember but it does need a mention. Back then AC Milan were still genuine contenders in Europe and boasted of quite a few star names. Spurs on the other hand weren’t exactly the high flying team they are now. In the first leg at San Siro, the Lilywhites managed to eke out a 1-0 win courtesy of a goal from Peter Crouch. A game that will be remembered more for the rash challenges (Mathieu Flamini) and Gennaro Gattuso’s confrontations. With a small advantage, the 2nd leg was basically Milan throwing everything at the home side but the star cast of Ibrahimovic, Seedorf, Robinho and Pato failed to bulge the net even once. Spurs held on to their lead and managed to get into the last 8.

4. Real Madrid - Lyon 2009/10 (Lyon won 2-1 on aggregate) -


Featuring for the 2nd time on the list Real Madrid had quite a dry run in the Champions League before 2014. They constantly failed to get past the early knockout rounds and this was one such instance. Jean Makoun’s spectacular strike in the first leg made sure Real Madrid had a job on their hands in the remainder of the tie. Parity was restored by Cristiano Ronaldo with an effort through the legs of Hugo Lloris but his now teammate, Miralem Pjanic would have the final say at the Santiago Bernabeu with his goal after a fantastic passing move. A certain Gonzalo Higuain did manage to hit the post with the goal open for taking before Pjanic’s killer blow.

5. Manchester United - FC Porto 2003/04 (FC Porto won 3-2 on aggregate) -


A match that would kick start one of English football’s greatest managerial rivalries. Jose Mourinho may have lost a bit of his sheen now but back then he was a bright and upcoming manager. His Porto side was due to square off against English giants Manchester United. Quinton Fortune tapped home a Paul Scholes freekick rebound off the bar to give United the lead. A brace from Benni McCarthy gave Porto an unexpected lead going into the 2nd leg. In the 2nd leg, United again got the first goal, this time it was Paul Scholes. What happened next sent Jose Mourinho into the higher echelons of football management. A mistake from Tim Howard would give Costinha the chance to tap it in at the dying embers of the game. Mourinho? He charged down the touchline in joy!


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