Over the last three decades, the UEFA Champions League knockout stage has produced some stunning shocks over the years. With this season’s newly formatted system, teams placed from 9th till 24th will play each other in the first knockout round to finalise the last eight teams for the Round of 16.
In this article, we take a look at the 5 biggest upsets in the UEFA Champions League first knockout round (Round of 16) over the years.
#5 Villarreal vs Juventus (agg: 4-1)
2021/22, Round of 16
Juventus were favourites to progress into the next round and got the perfect start when Dušan Vlahovi? recorded the quickest ever goal from a starting Champions League debutant with the opener after 33 seconds. But Daniel Parejo rescued a draw for Unai Emery’s underdogs before the return leg in Turin.
Gerónimo Rulli was the star of the show and kept the Yellow Submarine afloat in Turin before Villarreal produced an Italian-style three-goal counter-punch in the closing 12 minutes. Gerard Moreno tucked away his spot kick in the 78th minute to give Emery’s team the lead before Pau Torres put the game beyond doubt with a 85th minute goal. Arnaut Danjuma added gloss to the scoreline with a spot kick of his own in stoppage time.
Emery’s Villarreal carried on their giant killing spree by disposing off Bayern Munich in the quarterfinals before they succumbed to a 5-2 defeat on aggregate against Liverpool in the semi-final.
#4 Lyon vs APOEL (agg: 1-1, APOEL win 4-3 on pens)
2011/12 Round of 16
Having worked wonders to make it through the group stage, by becoming the first Cypriot side to reach the Round of 16, APOEL took it a step further.
Alexandre Lacazette’s 58th minute deflected goal gave Lyon a slim lead in the first leg with APOEL Nicosia showing no attacking intent – they did not have a shot until the 88th minute – and looked for much of the match like they might hang on.
Gustavo Manduca scored in the second leg to level the tie. Manduca was then dismissed in added time, but it made little difference as the match went to penalties. After Alexandre Lacazette had missed for Lyon and with APOEL scoring all their four kicks, Michel Bastos had to convert to keep the match going – but he failed with Dionissis Chiotis saving to his left to win the subsequent shoot-out.
APOEL drew Real Madrid in the quarterfinals with the Spanish club thumping them 8-2 on aggregate.
#3 Manchester City vs AS Monaco (agg: 6-6, Monaco win on away goals)
2016/17, Round of 16
Sergio Agüero and Radamel Falcao both scored twice as Manchester City and AS Monaco incredibly shared eight goals in the first leg of their Champions League last-16 encounter during the 2016/17 season. City won 5-3, despite trailing 2-1 and 3-2. Three goals in 11 minutes gave City a sizable lead on the night with a two-goal advantage.
However, the French club produced a scintillating performance in the return fixture with Kylian Mbappé and Fabinho giving them a 2-0 lead at half-time and winning on away goals. Leroy Sané gave City an important goal in the 70th minute, but it was a Tiemoué Bakayoko’s strike in the 77th minute that secured Monaco’s passage into the quarterfinals.
Monaco were the surprise package that season and would go on to play in the semifinals. They lost to Juventus 4-1 on aggregate over two legs.
#2 Manchester United vs Porto (agg: 2-3)
2003/04, Round of 16
Playing the first leg at home, José Mourinho’s Porto went behind before the 15-minute mark courtesy of a Quinton Fortune goal. However, the Portuguese champions fought back soon with South Africa’s Benni McCarthy scoring a volleyed goal in the 29th minute. Porto were dominant throughout the encounter and finally got the winner in the 78th minute thanks to McCarthy’s brilliant header.
To make matters worse, Manchester United had their skipper sent off in the 87th minute, missing the second leg.
In a must-win game, United had one foot in the quarter-finals after Paul Scholes fired them in front just after the half-hour mark at Old Trafford. But there was a late twist to this game. In the final minute of regulation time, Man Utd goalkeeper Tim Howard could only parry Benni McCarthy’s free-kick which was slotted in by Costinha from close range. José Mourinho’s ensuing run down the touchline to celebrate came to symbolise the shock outcome.
Mourinho and Porto’s fairytale run met its climax when the Portuguese club won their second European title with a 3-0 win over Didier Deschamps’ AS Monaco in the final.
#1 Ajax vs Real Madrid (agg: 5-3)
2018/19, Round of 16
Having won three back-to-back Champions League titles from 2016 to 2018, Spanish giants Real Madrid were the clear favourites heading into this Round of 16 encounter. Karim Benzema gave the Galacticos the lead in the Johan Cruijff ArenA on the hour mark before Hakim Ziyech leveled the score in the 75th minute. But it was Marco Asensio’s late first-leg winner that had the Merengues closing in on a ninth successive Champions League quarter-final.
However, Hakim Ziyech and David Neres tipped the tie upside down inside 20 minutes in the return leg.
Dušan Tadi? scored an outstanding goal in the second half to double Ajax’s lead on aggregate before Marco Asensio got one back for Los Blancos. Real’s hope for a comeback was cut short when Lasse Schöne scored an incredible free-kick in the 72nd minute to give them an unassailable 5-3 lead on aggregate.
Ajax made it to semifinals that season and were half an hour away from reaching the final before a second-half hat-trick by Tottenham Hotspur’s Lucas Moura turned the game upside down.
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