Arsenal have travelled to Portugal with the aim of keeping their Champions League dream alive, after Mikel Arteta’s side endured back-to-back disappointments in domestic cup competitions.
The Gunners were hoping to respond to their Carabao Cup final defeat in the FA Cup on Saturday, but were stunningly beaten 2-1 by Championship side Southampton in the last eight.
Defeat has piled more pressure onto their Champions League campaign, with Arteta’s side hoping to maintain their unbeaten record in this season’s competition when they face Sporting Lisbon.
Arsenal are still yet to lift the famous trophy, despite featuring in the competition in 22 of the last 28 editions, which has included reaching the final in 2006 and being eliminated in the semi-final twice.
The Gunners’ two most recent campaigns have showed signs of promise, but Arsenal have endured the too familiar feeling of crashing out in the knockout stages.
With Arsenal currently bookmakers’ favourites to win this year’s competition, Daily Mail Sport takes a look at some of their most devastating Champions League exits.
Arsenal are hoping to banish their previous Champions League heartbreaks as they bid to win the competition for the first time
1998/99 – Group stage
Having won the Premier League the previous season, the Gunners’ inaugural Champions League campaign saw them crash out at the first hurdle.
Arsenal boss Arsene Wenger had admitted switching their home matches to Wembley was a gamble, as the Gunners looked to benefit from larger crowds than they would have had at Highbury.
In a group made up of Lens, Dynamo Kyiv and Panathinaikos, Arsenal took just eight points from six games, which saw them finish third in the group.
2000/01 – Quarter-finals
The 2000/01 campaign saw Arsenal reach the knock-out stages of the Champions League for the first time, after getting through the competition’s then two group stages.
The Gunners won their first group courtesy of having a better head-to-head record than Lazio, after winning four, drawing one and losing one of their matches.
It was a similar story in the second group phase, as they ended as runners-up to Bayern Munich but edged into the quarter-finals due to their head-to-head record against Lyon. Both teams had won two, drawn two and lost two.
Arsenal were, however, eliminated in the last eight by an impressive Valencia side that would go on to finish as runners-up, losing the final on penalties to Bayern.
Ray Parlour’s first leg screamer had seen Arsenal win the first leg 2-1 at Highbury, but they were undone away from home.
Valencia forward John Carew scored a glancing header with 15 minutes remaining of the second leg, sending Valencia through via the away goals rule.
Arsenal were knocked out by Valencia on away goals in the 2000-1 Champions League
2003/04 – Quarter-finals
With the second group phase’s removal in 2003, Arsenal progressed to the last-16 following three wins in the group stage.
A clash with Celta Vigo came next and Wenger’s team came out 5-2 winners on aggregate, as Thierry Henry netted a brace in the second leg.
Chelsea, however, brought the Gunners campaign to a close in the quarter-finals.
In what was a hard-fought encounter, Arsenal held a 2-1 advantage on aggregate at half-time in the second leg. The Gunners were unable to make home advantage the difference with 45 minutes to play.
A Jens Lehmann mistake gifted Frank Lampard a Chelsea equaliser, before Wayne Bridge’s 87th minute strike sealed a dramatic victory for the Blues.
Arsenal were left to ponder what could have been with FC Porto ultimately lifting the trophy in what was a historic season for the Portuguese side.
Wayne Bridge’s late winner saw Chelsea eliminate Arsenal in the 2003-04 quarter-finals
2005/06 – Final
Arsenal’s most devastating defeat came in 2006 having finally navigated their way to the final, eliminating some of Europe’s biggest hitters in the process.
An unbeaten group phase meant they faced Spanish giants Real Madrid in the round of 16. Thierry Henry scored a famous winner in a 1-0 victory in Madrid, with Arsenal preserving the slender advantage in the second leg.
Next up was a meeting with Juventus. The Gunners’ resolute defence kept two clean sheets, with goals from Cesc Fabregas and Thierry Henry being enough to see Arsenal progress further than they ever had done previously.
Villarreal enjoyed a surprisingly successful Champions League campaign and faced the Gunners in the semi-final.
Another two clean sheets over two legs and a Kolo Toure goal saw Arsenal through to the final.
Juliano Belletti scored the winner as Barcelona beat Arsenal in the 2006 Champions League final
Finishing as runners-up in 2006 remains the closest Arsenal have come to winning the competition
Arsenal looked on course for a maiden Champions League title after Sol Campbell gave them the lead in the final against Barcelona in Paris.
The opening goal had come despite Arsenal being reduced to 10-men, after Jens Lehmann was sent off bringing down Samuel Eto’o just 18 minutes into the final.
Barcelona eventually broke down Arsenal’s resilient defence, with Henrik Larsson proving key to turning the final in their favour.
The substitute provided the assist for Eto’o’s equaliser, before creating Juliano Belletti’s 81st minute winner.
In a campaign in which the Gunners only conceded four goals throughout the entire competition, they ultimately came up agonisingly short.
2006/07 – Round of 16
Arsenal found themselves in unusual territory after a fourth place finish domestically the preceding season.
They were forced to enter through the qualifying rounds, and did so, beating Dynamo Zagreb.
Passing through the group stage, Arsenal met PSV in the last-16.
Having trailed 1-0 from the first leg, Arsenal were gifted an equaliser when PSV defender Alex put through his own net.
The Brazilian, who was on-loan from Chelsea, made amends by scoring at the other end to send Arsenal to a shock 2-1 defeat on aggregate.
The result meant Arsenal had endured a nightmare 10 days, having lost the League Cup final, suffered an FA Cup defeat by Blackburn and then crashed out of the Champions League.
Arsenal were surprisingly dumped out by Dutch side PSV in the last-16 in 2006-07
2007/08 – Quarter-finals
The Gunners breezed through a qualifying round and the group stage in the 2007/08 campaign, before being drawn against AC Milan in the last-16.
Wenger’s side became the first English side to beat AC Milan in the San Siro, with Fabregas and Emmanuel Adebayor scoring late to earn a 2-0 aggregate win.
Arsenal would exit the competition in the quarter-finals after a classic second leg against Liverpool at Anfield.
A 1-1 draw in the first leg had set the tie perfectly poised for the return fixture on Merseyside.
The match did not disappoint, with Arsenal taking the lead with Abou Diaby and Liverpool responding through Sami Hyypia.
After Fernando Torres put Liverpool ahead on the night, Arsenal responded through Adebayor to lead the tie on away goals.
Two minutes later, a foul by Kolo Toure on Ryan Babel gave Liverpool the chance to go back ahead, with Steven Gerrard taking the opportunity from the penalty spot.
Arsenal’s fate was sealed when Babel put Liverpool 4-2 up at Anfield, with the hosts eventually sealing a 5-3 aggregate win.
A penalty proved crucial as Liverpool overcame Arsenal in the 2008 quarter-finals
Steven Gerrard scored from the spot as Liverpool earned a 5-3 aggregate victory
2008/09 – Semi-finals
Arsenal’s second appearance at this stage of the competition saw only more misery, with another defeat at the hands of a domestic rival.
A young Arsenal side had not been deterred by the shortcomings of the previous season, after a comfortable group stage was followed by a penalty shoot-out win against Roma in the last-16.
Familiar opposition, Villarreal, were toppled by the Gunners in the quarter-finals to set up an all-English semi-final against Manchester United.
Sir Alex Ferguson’s team proved far too strong, as they recorded a 4-1 aggregate victory over the Gunners.
The second leg was famed for Cristiano Ronaldo’s stunning early free kick from range, as well as a breathtaking counter attacking goal for his second of the night.
Cristiano Ronaldo’s long-range free kick helped Man United beat Arsenal in the 2009 semi-final
Ronaldo also scored from a stunning counter-attack as Man United proved too strong
2016/17 – Round of 16
Arsenal’s 2016/17 campaign ended in their most humiliating European defeat to date.
The Gunners topped the group for the first time in five years, with Mesut Ozil’s iconic winner in Ludogorets a highlight.
Bayern Munich awaited them in the last-16, and the Bundesliga giants showed no mercy.
A 5-1 win for the home side in Munich put Arsenal out of sight for the reverse fixture, yet Bayern made totally sure by doubling their tally at the Emirates, running out 10-2 aggregate victors.
It would prove to be Wenger’s final Champions League tie in charge of the Gunners, who would have to wait seven years to return to Europe’s elite club competition.
Bayern Munich thrashed Arsenal 10-2 on aggregate in the last-16 back in 2017
It would prove to be Wenger’s last Champions League tie in charge of Arsenal as the Gunners endured a long spell out of the competition
2023/24 – Quarter-finals
The Gunners were haunted by Bayern Munich again on their return to Champions League football, after Arsenal reached the quarter finals for the first time since 2010.
Porto had taken Mikel Arteta’s side to penalties in the last-16, but Arsenal narrowly progressed to set up a reunion with Bayern.
A thrilling first leg saw honours even at 2-2 heading into the reverse leg in Munich.
Bayern captain Joshua Kimmich ended Arsenal’s campaign by earning the German giants a 1-0 win in the second leg.
2024/25 – Semi-finals
In the first year of the revamped league phase, Arsenal finished third by winning six out of eight matches, earning an automatic spot in the last-16.
The Gunners dismantled PSV 9-3 overall to book their place in the quarter-finals, setting up a tie with Real Madrid.
Two historic nights followed in North London and Madrid respectively. Declan Rice scored two stunning free-kicks at the Emirates with Mikel Merino adding a third.
Eventual winners PSG ended Arsenal’s Champions League campaign in last year’s semi-finals
The Gunners were beaten 3-1 on aggregate by the French giants after a memorable campaign
Bukayo Saka and Gabriel Martinelli then both scored at the Bernabeu in a 2-1 win, with Arteta’s side winning 5-1 on aggregate.
The performances raised hopes Arsenal could go on to win the Champions League, but PSG proved too strong in the semi-finals.
Arsenal lost 1-0 at home and 2-1 away to exit the competition, with PSG ultimately going on to lift the famous trophy for the first time.
