From Van Persie red to Messi magic: Arsenal's most painful Champions League nights

[p]Since making their Champions League debut in the 1998/99 season, the [a href="https://www.flashscore.ca/team/arsenal/hA1Zm19f/"]Gunners[/a] have played 225 matches in the competition, holding the record for the most matches of any team to have never lifted the trophy.[/p][p]Across 23 campaigns in Europe's elite competition, Arsenal have reached three semi-finals and played in only one final, losing to [a href="https://www.flashscore.ca/team/barcelona/SKbpVP5K/"]Barcelona[/a] in 2006.[/p][p]Ahead of the [a href="https://www.flashscore.ca/game/soccer/arsenal-hA1Zm19f/psg-CjhkPw0k/?mid=EJZRaQ15"]Champions League final[/a] on Saturday, [i]Flashscore[/i] looks back at eight of their most agonising defeats as they look to finally land their hands on Europe's most coverted trophy.[/p][h2]Barcelona 3-1 Arsenal: Round of 16, 2011 [/h2][p]Arsenal striker [a href="https://www.flashscore.ca/player/van-persie-robin/0vgcq6un/"]Robin van Persie[/a] described the referee's decision as a "joke" while manager Arsene Wenger called it "embarrassing".[/p][p]The Gunners arrived at the Camp Nou holding a 2-1 advantage, and with the score level at 1-1 on the night, referee Massimo Busacca blew for an offside against Van Persie.[/p][p]Already booked earlier for a challenge on Dani Alves, the Dutch striker went on to take a shot at goal moments after the whistle and was immediately shown a second yellow card for time-wasting.[/p][p]Reduced to 10 men, Arsenal eventually fell to a 3-1 defeat, crashing out of the competition 4-3 on aggregate.[/p][p][b]"If there were four, five, six seconds in between (the whistle and the shot), you can make a check for offside. One second? It's a joke,"[/b] van Persie said.[/p][p][b]"I tried to explain there were 95,000 people jumping up. How can I hear the whistle?"[/b][/p][image alt="Arsene Wenger reacts as Robin van Persie is sent off" id="dd5842e0-a93a-44de-b662-31d866672dc5" credit-line="Back Page Images / Shutterstock Editorial / Profimedia" guid="892ba13b-42bf-4ef7-8a54-6316fa680f6b" original-width="1400" original-height="1043" /][h2]Arsenal 1-2 Chelsea: Quarter-final, 2004 [/h2][p]A dramatic late strike from [a href="https://www.flashscore.ca/player/bridge-wayne/fyXzTdMR/"]Wayne Bridge[/a] stunned Highbury and sent Chelsea into the Champions League semi-finals during Arsenal's historic Invincible league season.[/p][p]After the first leg ended 1-1, Arsenal took control when Jose Antonio Reyes fired the hosts ahead shortly before half-time. But [a href="https://www.flashscore.ca/player/lampard-frank/GWpe9c0q/"]Frank Lampard[/a] struck after the break to bring Chelsea level.[/p][p]With extra time looming, Bridge charged into the penalty area and drilled a low finish beyond goalkeeper [a href="https://www.flashscore.ca/player/lehmann-jens/rahgtmBn/"]Jens Lehmann[/a] to send Claudio Ranieri's side through 3-2 on aggregate.[/p][p]Chelsea's European run would end in the semi-finals against Monaco, before Jose Mourinho's Porto ran out shock winners. It was a huge opportunity missed for the Gunners.[/p][embed guid="acc30dd0-50c7-41e6-b237-3b2ddd64a2bf" url="https://www.youtube.com/watch?v=Wh5UNGtI-FY" social-type="youtube" /][h2]Arsenal 1-3 Man Utd: Semi-final, 2009 [/h2][p]Arsenal's first-ever home Champions League semi-final turned into a nightmare as Premier League rivals [a href="https://www.flashscore.ca/team/manchester-united/ppjDR086/"]Man Utd[/a] ran riot in North London.[/p][p]Trailing 1-0 from the first leg, Arsenal entered the Emirates full of belief after manager Arsene Wenger promised a "magnificent" performance. [/p][p]But any hopes of a famous European comeback were shattered by a devastating first-half display by the defending champions.[/p][p][a href="https://www.flashscore.ca/player/park-ji-sung/0vLDaBdI/"]Ji-Sung Park[/a] opened the scoring for Sir Alex Ferguson’s side after just eight minutes before [a href="https://www.flashscore.ca/player/ronaldo-cristiano/WGOY4FSt/"]Cristiano Ronaldo[/a] thumped home a 40-yard free-kick three minutes later.[/p][p]The Portuguese star added to Arsenal's woe with his second goal of the night to make it 3-0 after the break before [a href="https://www.flashscore.ca/player/fletcher-darren/j3pIFABB/"]Darren Fletcher[/a] was sent off midway through the second half.[/p][p]Despite Arsenal's Van Persie scoring a consolation goal moments later, United were rarely troubled as they punched their ticket to face Barcelona at Wembley 4-1 on aggregate.[/p][embed guid="c65edb7a-7d05-4acb-ba39-99167e2899b2" url="https://www.youtube.com/watch?v=mxWIy8q_vQw" social-type="youtube" /][h2]Barcelona 4-1 Arsenal: Quarter-final, 2010 [/h2][p][a href="https://www.flashscore.ca/player/messi-lionel/vgOOdZbd/"]Lionel Messi[/a] scored all four goals as the Gunners were torn apart by a ruthless Barcelona side who progressed 6-3 on aggregate. [/p][p]Arsenal's [a href="https://www.flashscore.ca/player/fabregas-cesc/YXIDwoe5/"]Cesc Fabregas[/a] famously broke his leg after crashing home a penalty to level the first leg 2-2, but the Gunners found themselves totally outclassed by Pep Guardiola’s side in Catalonia.[/p][p][a href="https://www.flashscore.ca/player/bendtner-nicklas/UaKqoH09/"]Nicklas Bendtner[/a] briefly gave the visitors hope with the opener in the 18th minute, but Messi took complete control of the tie with a devastating first-half hat-trick before adding a fourth late on.[/p][p][b]"We lost to a team who are better than us and against the best player in the world,"[/b] manager Arsene Wenger said. [/p][p][b]"When there's players like Messi then you can pay for any mistake. Once he's on the ball, he's unstoppable."[/b][/p][embed guid="771f677c-959f-40e1-bd43-ef68b59b87c6" url="https://www.youtube.com/watch?v=-kWIh_9sVT8" social-type="youtube" /][h2]Monaco 3-3 Arsenal: Last 16, 2015 [/h2][p]Arsenal's hopes of reaching the last eight for the first time in five years were left in tatters after a disastrous first-leg display that manager Arsene Wenger branded "suicidal".[/p][p]The performance was so chaotic that the BBC said the Gunners had "plumbed the depths of incompetence and naivety".[/p][p]Monaco opened the scoring through [a href="https://www.flashscore.ca/player/kondogbia-geoffrey/nZs03zT2/"]Geoffrey Kondogbia[/a]'s deflected strike and doubled their advantage in front of a shell-shocked Emirates through former Tottenham striker [a href="https://www.flashscore.ca/player/berbatov-dimitar/KjMNbKF1/"]Dimitar Berbatov[/a].[/p][p][a href="https://www.flashscore.ca/player/oxlade-chamberlain-alex/WzNLf7VR/"]Alex Oxlade-Chamberlain[/a] briefly reignited hope with a goal for the Gunners, but [a href="https://www.flashscore.ca/player/carrasco-yannick/lzccuuAC/"]Yannick Carrasco[/a] broke clear to add a third late on.[/p][p]Arsenal launched an all-out assault in the return leg, but a famous comeback ultimately fell agonisingly short as they could only win 2-0 and crashed out on away goals.[/p][embed guid="9a04195d-a56b-4bdb-9764-c9294e5cecc4" url="https://www.youtube.com/watch?v=GHUE4Jmwkqk" social-type="youtube" /][h2]Bayern Munich 1-0 Arsenal: Quarter-final 2024 [/h2][p]Arsenal have endured a painful history against [a href="https://www.flashscore.ca/team/bayern-munich/nVp0wiqd/"]Bayern[/a] in the Champions League, suffering 5-1 defeats in the 2015 group stage and in both legs of their infamous last-16 tie in 2017. Yet it was the heartbreak of 2024 that perhaps cuts deepest.[/p][p]After earning a hard-fought 2-2 draw in the first leg at the Emirates, confidence was growing that Arsenal could finally reach the last four -  boosted further by Bayern surrendering their Bundesliga title to Bayer Leverkusen in the days leading up to the match.[/p][p]But the Allianz Arena once again proved a miserable destination for the Gunners.[/p][p][a href="https://www.flashscore.ca/player/goretzka-leon/l2JpsMjB/"]Leon Goretzka[/a] hit the bar and [a href="https://www.flashscore.ca/player/guerreiro-raphael/ImhgOoOl/"]Raphael Guerreiro[/a] clipped the post before [a href="https://www.flashscore.ca/player/kimmich-joshua/MkMrkZLc/"]Joshua Kimmich[/a] rose highest to head home a Guerreiro cross to send the Germans into the semi-finals against Real Madrid.[/p][embed guid="5df7812e-ae5f-43b6-be25-90ec4204eaf8" url="https://www.youtube.com/watch?v=Z3Ec5x5iz7Q" social-type="youtube" /][h2]Valencia 1-0 Arsenal: Quarter-final, 2001 [/h2][p]Arsenal suffered heartbreak in Spain as [a href="https://www.flashscore.ca/team/valencia/CQeaytrD/"]Valencia[/a] knocked the Gunners out on away goals.[/p][p]There was growing optimism before kick-off that Arsenal could setup all-English semi-final against Leeds after leading the first leg 2-1, but Arsene Wenger's side were ultimately punished by their profligacy in front of goal.[/p][p][a href="https://www.flashscore.ca/player/carew-john/2ByRbYER/"]John Carew[/a]'s header 15 minutes from time stunned the away fans as Arsenal's hopes of reaching the last four came crashing down at the Camp de Mestalla.[/p][p]The tie ended 2-2 on aggregate with Valencia progressing on away goals.[/p][image alt="Valencia forward John Carew battles past Arsenal captain Tony Adams" id="a30cdb1d-9195-4ebb-8530-34238560cf93" credit-line="Christophe Simon / AFP / AFP / Profimedia" guid="d8d816ef-0659-435d-a2f5-d654b066d981" original-width="1400" original-height="1120" /][h2]Barcelona 2-1 Arsenal: Final, 2006 [/h2][p]So close but so far for Arsenal, who came within touching distance of European glory at the Stade de France in Paris, only to suffer heartbreak in their maiden Champions League final.[/p][p]Disaster struck after just 18 minutes when goalkeeper [a href="https://www.flashscore.ca/player/lehmann-jens/rahgtmBn/"]Jens Lehmann[/a] was sent off for bringing down the advancing [a href="https://www.flashscore.ca/player/eto-o-samuel/KUCt6uhi/"]Samuel Eto'o[/a], but [a href="https://www.flashscore.ca/player/campbell-sol/8GIb5AxG/"]Sol Campbell[/a] gave 10-man Arsenal hope after scoring the opening goal shortly before the break.[/p][p]Barça’s relentless pressure eventually told in the second half as two goals inside the final 15 minutes from Eto’o and [a href="https://www.flashscore.ca/player/belletti-juliano/f9vmqdyL/"]Juliano Beletti[/a] sealed a remarkable comeback to send their fans into raptures and break Arsenal's hearts.[/p][embed guid="66136937-23ea-4b50-ac39-c08fdb537b46" url="https://www.youtube.com/watch?v=rQrz84zKVvI" social-type="youtube" /][p]Lehmann was at Selhurst Park on Sunday to see Arsenal lift the Premier League trophy for the first time in 22 years, and offered advice to fellow number one [a href="https://www.flashscore.ca/player/raya-david/nkVV0IXb/"]David Raya,[/a] who is set to start the Champions League final against PSG this weekend.[/p][p][b]"Don't get sent off!"[/b] he said.[/p][embed guid="2803e660-d004-4aeb-8bc8-3eeda30a797e" url="https://www.youtube.com/watch?v=oiYVFQmqAZc" social-type="youtube" /][h2]Arsenal’s Champions League / European Cup record[/h2][p]2025/26: Finalists [/p][p]2024/25: Semi-final [/p][p]2023/24: Quarter-final [/p][p]2016/17: Round of 16 [/p][p]2015/16: Round of 16 [/p][p]2014/15: Round of 16 [/p][p]2013/14: Round of 16 [/p][p]2012/13: Round of 16 [/p][p]2011/12: Round of 16 [/p][p]2010/11: Round of 16 [/p][p]2009/10: Quarter-finals [/p][p]2008/09: Semi-finals [/p][p]2007/09: Quarter-finals [/p][p]2006/07: Round of 16 [/p][p]2005/06: Final [/p][p]2004/06: Round of 16 [/p][p]2003/04: Quarter-final [/p][p]2002/03: Second group stage [/p][p]2001/02: Second group stage [/p][p]2000/01: Quarter-final [/p][p]1999/00: First group stage [/p][p]1998/99: Group stage [/p][p]1991/92: Second round [/p][p]1971/72: Quarter-finals[/p]