The Biggest Shocks in the History of the Champions League Round of 16

Grant McQuillan

Barcelona 6-1 PSG (6-5), 2017

When Paris Saint-Germain absolutely demolished Barcelona 4-0 at the Parc des Princes, it was thought that the tie was over as Barcelona didn’t look at all threatening in the game and were trounced by a sensational PSG side with former Real Madrid man, Angel Di Maria, running the show.

However, the second leg started as if Barcelona were on a mission to stop all doubt, with Luis Suarez scoring after three minutes to give them the perfect start, before they took a 2-0 lead into half time. People thought the tie was over, however, when Edinson Cavani netted an away goal which meant Barcelona had to score six to advance (four more at the time), and that all but seemed impossible for any club, never mind one that contained Lionel Messi, Suarez, and Neymar

They pull another back though, and two minutes to go in normal time, Barcelona still needed to score three goals and fans were leaving the ground still as the pure mathematics of the equation itself seemed near impossible.

Two goals in the next five minutes brought the eyes of the world upon the Nou Camp as the most dramatic European knockout tie in history was taking place, and a goal in the 95th minute from Sergi Roberto sent Barcelona would end up sealing the deal.

Probably the greatest game in round of 16 history.

PSG 1-3 Manchester United (3-3 - United win on away goals), 2019

Fast forward two years, however, and times were different for PSG.

With and 10 first team players unavailable, and a 2-0 deficit with away goals, Manchester United were huge underdogs going into this game at the Parc des Princes with PSG already looking ahead to the quarter-finals.

Despite a much weaker team, United started the game very strong, with Romelu Lukaku scoring after two minutes, and despite PSG levelling the score, Lukaku got a second away goal to cancel out PSG’s from the first leg in a fantastic attacking display from Ole Gunnar Solskjaer's men.

The whole second half had both sets of fans on edge, knowing how much the next goal meant, but with the game dwindling down, it looked as if PSG were going to survive the scare, but United were awarded a penalty in a stunning VAR call on Pascal Kimpembe only for Marcus Rashford to score deep into stoppage time.

Real Madrid 1-4 Ajax (3-5), 2019

Off the back of winning three straight Champions League titles and winning the first leg 2-1 in Amsterdam, it looked as if the second leg was a formality for Real Madrid, but Ajax had different ideas.

Two goals in the first 20 minutes showed that they were there to cause the upset, and adding a third after an hour showcased their quality with them dominating the reigning champions in their own stadium.

After scoring a goal in the 70th minute, there was still a chance Real could use their experience to come back, but a goal just two minutes later by Ajax shut that down and the Dutch giants racked up one of their greatest ever Champions League victories.

Manchester United 1-1 FC Porto (2-3), 2004

Even after winning the first leg in Portugal, Porto was still counted out in this tie, with Sir Alex Ferguson's Manchester United the massive favourites over Jose Mourinho’s Porto.

Paul Scholes scored after half an hour and looked to send United through to the next round on away goals, with them keeping the lead right up until the end of the game.

Porto’s Francisco Costinha benefited from a mistake from Tim Howard, where he just had to tap the ball in from a few yards out, to send underdogs Porto into the next round and Jose Mourinho down the Old Trafford sideline. It started "The Special One's" era and a period of three years without a Premier League for United as Mourinho would go on to win the Champions League with Porto and then take over England with Chelsea next season.

Arsenal 2-1 Barcelona (3-4), 2011

Arsenal were huge underdogs going into the game at the Emirates with Barcelona the heavy favourites for the title itself with one of the best squads ever assembled, whereas Arsenal had an 18-year-old Jack Wilshere in midfield that was relatively unknown compared to the famous midfield in front of him: Sergio Busquets, Xaxi, and Andreas Iniesta.

Barcelona took the lead in the 26th minute through David Villa and it felt like they were going to eventually add more goals, but Jack Wilshere had the performance of a lifetime which saw the game shift the other way.

Wilshere held his own against that unrivalled modern day midfield trio of Busquets, Xaxi and Iniesta, and led Arsenal to score two late goals in the game to complete a stunning comeback where Andrei Arshavin netted a famous winner.

Wilshere's display remains probably the best performance by an English teenager in the Champions League since Wayne Rooney's debut against Fenerbahce.


⚽️ GET £30 IN FREE BETS WHEN YOU PLACE A £10 BET ⚽️
New customers only. First single & e/w bet only odds of 1/1 or greater. 3 x £10 bet tokens. Free bet stakes are not included in returns. Free bets are only redeemable on football. Free bets are non-withdrawable. No free bet expiry. Eligibility restrictions and further t&cs apply. 18+.
Claim Bonus
🟢 Bet £10 & Get £50 in free bets! 🟡
For new customers. Min deposit requirement. Free Bets are paid as Bet Credits and are available for use upon settlement of qualifying bets. Min odds, bet and payment method exclusions apply. Returns exclude Bet Credits stake. Time limits and T&Cs apply.
Claim Bonus
🔸 BET £10 AND GET £30 IN FREE BETS! 🔸
New Customer offer. Place a min £10 bet on the Sportsbook on odds of min 1/2 (1.5), get £30 in Free Bets. Rewards valid for 30 days. SMS verification required. Only deposits via cards will qualify. T&Cs apply. Please Gamble Responsibly
Claim Bonus
⚽️ BET £10 & GET £40 IN FREE BETS! (MOBILE ONLY) ⚽️
Sign-up via Mobile using promo code N40 and place a bet of £10/€10 or more and we will give you 4x £10/€10 free bets. By entering the Promo code in the box above you agree to the full terms and conditions of this promotion as displayed below. See full terms below.
Claim Bonus
⚽️ UP TO £50 MONEY BACK AS CASH IF ANY OF YOUR FIRST 5X £10 FOOTBALL BETS LOSE ⚽️
Place 5x£10 Sportsbook bets on any market at minimum odds of 2.0 (Evs), and get money back as Cash if it loses. Max refund per qualifying bet is £10 (up to £50 in total). Only deposits made via Cards will be eligible for the promotion (Apple Pay excluded). T&Cs apply
Get Offer
🔷 GET £30 IN FREE BETS WHEN YOU BET £10 🔷
Full T&C’s Apply. New customers on mobile only. 7 days to claim and stake £10 minimum bet at odds of 1.5 or greater to qualify. Free, void, cashed out or partially cashed out bets do not qualify. Max 3x £10 free bets credited on bet settlement. Free bets must be used on 4 or more selections with selection odds of 1.3 or greater. Free bets are non-withdrawable and stake not returned with winnings. 7 day expiry. 18+ BeGambleAware.org.
Claim Bonus
🟠 BET £10 & GET £20 IN FREE BETS! 🟠
*New members. £10 min deposit & bet on sportsbook, placed & settled at 1.5 min odds within 14 days of sign-up. Win part of E/W bets. 2 non-withdrawable £10 Free Bet Tokens: accept in 7 days, valid for 7 days from crediting (ex. E/Ws & Multiples), stakes not returned. Click here for Rules & Exclusions. Bet Responsibly. BeGambleAware.org
CLAIM HERE
🔴 GET £20 IN FREE BETS WHEN YOU BET £5 🔴
18+ New UK+IRE Customers only. Certain deposit methods & bet types excl. Min first £/€5 bet within 14 days of account reg at min odds 1/2 to get 4x £/€5 free bets. Free bets valid for 7 days, stake not returned. Restrictions + T&Cs apply.
Claim Bonus
🟩 BET £10 & GET £30 IN FREE BETS 🟩
New UK, IE & Malta customers only. 18+. Min £10/€10 first deposit using Debit Card or Trustly. Place a bet of £10 at min odds of 1.5. Free bets expire in 90 days. Full T&Cs apply.
Claim Bonus
🔹 GET £30 IN BONUSES WHEN YOU BET £5 🔹
18+ New customers only. Opt in, bet £5 at odds 2.00+ within 7 days of registering, no cashout. Get 2x £10 Free Bets, set events at odds 2.00+. Plus a £10 Slot Bonus, selected games, wager 20x to withdraw max £250. 7 day bonus expiry. Card payments only. T&Cs apply, see below. begambleaware.org | Please gamble responsibly
Claim Bonus
⚜️ GET A FREE BET UP TO £35 + 10 FREE SPINS ⚜️
If your account has Sportsbook losses at the end of your first day's betting, QuinnBet will refund 50% of your losses as a Free Bet up to £35 (min 3 bets) Plus 10 Free online casino spins at QuinnCasino. Even if your account is up, you're guaranteed a £5 Free Bet Plus 10 Free Spins provided you place at least 1 bet of £10 or greater at the minimum odds. T&Cs apply | 18+ New UK Customers Only | BeGambleAware.org
Claim Bonus
🕋 BET £5 & GET £30 IN BONUSES 🕋
18+ New Customers opt in, bet £5 & get 2x £10 Free Bets for set events (odds 2.00+) + £10, Slots Bonus, selected games, 35x wagering to withdraw max £250. Bonuses expire in 7 days. Card Payments only. T&Cs Apply, see below. | begambleaware.org | Please gamble responsibly
Claim Bonus
🟣 BET £10 & GET £60 FREE BETS! 🟣
New UK customers only. Register using the promo code BETFRED60, deposit and place first bet of £10+ on Sports (cumulative Evens+). First bet must be on Sports. £20 in Free Bets to be used on Sports, £10 in Free Bets to be used on Lotto and 50 Free Spins (20p per spin) credited within 48 hours of bet settlement. Further £20 in Free Bets credited 5 days after settlement. Bonuses have a 7-day expiry. Payment restrictions apply. SMS verification and/or Proof of I.D and address may be required. Full T&Cs apply.
Claim Bonus
🟢 UP TO £40 MONEY BACK AS BONUSES + A £10 CASINO BONUS 🟢
18+ begambleaware.org. New customers only. Min deposit £10. Money back as bonus if first sports bet loses. Wagering requirements: sportsbook 3x at min. odds of 1.40 (2/5), casino 50x. Unless forfeited the sportsbook bonus must be wagered before using the casino bonus. Bonus expires 7 days after opt-in. Visit Unibet.co.uk for full T&C's. #Ad
Claim Bonus
🔵 BET £10 & GET £20 IN FREE BETS + ACCA REWARDS OF YOUR CHOICE! 🔵
New UK customers (Excluding NI) only. Mobile exclusive. Min stake £10. Min odds Evs. Free bet applied on 1st settlement of any qualifying bet. 30 days to qualify. Free bets expire in 7 days. Cashed out/Free Bets won’t apply. Payment method restrictions. 1 Free Bet offer per customer, household & IP Address only. 18+. T&C's Apply **18+. Choose either Boost or Insurance. Available for in-play/pre-match bets on selected sports. You cannot use specials, boosts, any free bet or any other promotion. A minimum of 5 selections and minimum odds of 1/5 per selection/leg to receive Acca Rewards. Minimum stake of £/€0.05. Max free bet refund of £/€20 per Acca for Insurance. Maximum bonus payout is €/£1,000 per Acca for boost. Free bets, cashed out or voided bets will not qualify for this promotion. T&Cs apply.
Claim Bonus
♥️ GET £40 FREE PLAY PLUS A £10 FREE SPORTS BET! ♥️
1st time depositors only. Min. deposit £10. Use code FAPOKER. Free Play given as cash, Spin & Go tickets, and a Sports Free Bet over 6 days. Tickets expire after 24 hours. Withdrawal restricted during bonus period. Terms apply.
Claim Bonus
🔵 GET £20 IN FREE BETS WHEN YOU BET £5 🔵
18+ New UK & ROI Customers only. Min deposit £5. Min first £5 bet at minimum odds 1/2 to qualify for 1x 20 free bet. Certain deposit methods and bet types excl. Free bet valid for 7 days, stake not returned. Restrictions + T&Cs apply.
Claim Bonus
⚫️ GET A £30 MATCHED FREE BET IF YOUR FIRST FOOTBALL ACCA LOSES!!!! ⚫️
*New UK customers only. Min Deposit: £5. Maximum Free Bet: £30. First bet on a Football multiple with 3+ selections. Overall odds: 3.00 (2/1) or higher. Free Bets available upon settlement of the qualifying bet. Debit card deposits only. This is offer is valid for 7 days from your new account being registered. 18+ BeGambleAware.org Full terms apply.
Claim Bonus