Ranked! Arsene Wenger’s 10 most defining moments at Arsenal

Wenger's defining moments

After 22 years at the helm, Arsene Wenger will step down as Arsenal manager at the end of the season. The Gunners stopped contending for the game’s major prizes during the second half of the Frenchman’s tenure, but Wenger brought great success to north London during his first decade at the helm.

In this slideshow, we pick out the 10 most defining moments of Wenger’s Arsenal career – some good, some bad.

10. A very good Friday: Arsenal 4-2 Liverpool, Apr 2004

The mood was tense ahead of Arsenal’s Good Friday meeting with Liverpool in 2004. The Gunners had endured torrid week, exiting the FA Cup at the hands of Manchester United and the Champions League after defeat by Chelsea. Still unbeaten in the league, Arsenal simply had to beat Liverpool to keep their campaign on course.

Despite trailing 2-1 at half-time to goals from Sami Hyypia and Michael Owen, the sublime Thierry Henry fired the hosts to a rousing second-half comeback, with his sensational slaloming second goal the highlight of a 4-2 triumph.

9. Demolition derby: Arsenal 3-1 Spurs, Nov 1996

Two months after being appointed Arsenal boss in September 1996, the scholarly Wenger prepared for his first north London derby. Having already changed the players' diets, stretching habits and warm-ups, his team faced Tottenham in an almost biblical downpour at Highbury. 

With the scores level after 85 minutes (George Graham would surely have instructed his team to secure the draw), the Gunners continued to swarm forward. Tony Adams volleyed Arsenal into the lead, before Dennis Bergkamp delivered the perfect injury-time coup de grace, curling in a superb effort to make it 3-1.

8. The cup that cheers: Arsenal 3-2 Hull, May 2014

Their title ambitions may have crumbled but in May 2014, after nine long years, Arsenal finally ended their trophy drought at Wembley by defeating Hull in the FA Cup Final. 

In typical fashion, Arsenal made heavy weather of the final and went 2-0 down in the opening eight minutes. Santi Cazorla halved the deficit nine minutes later and Laurent Koscielny drew the Gunners level on 71 minutes, paving the way for Aaron Ramsey to score a late winner and send relieved Arsenal fans into raptures. 

7. Down and out: Arsenal 1-2 Liverpool, May 2001

"When will this team win another trophy?" ITV's Gary Newbon asked Gunners skipper Patrick Vieira after Arsenal somehow snatched defeat from the jaws of victory in the 2001 FA Cup Final against Liverpool at the Millennium Stadium. 

For the third consecutive campaign, the Gunners – who took the lead through Freddie Ljungberg and missed a hatful of other chances – had failed to land silverware, and their defensive fragility was painfully evident.

Michael Owen’s two late goals prompted calls for Arsenal’s ageing defence to be dismantled, and Vieira flirted with Real Madrid in the off-season. But he, Adams, David Seaman and Lee Dixon were far from done at Highbury.

6. Money, money, money: Arsenal 1-2 Chelsea, Apr 2004

For all of Arsenal fans' chants about sticking Russian money up certain orifices, there was no hiding the significance of newly moneyed Chelsea's victory in the 2004 Champions League quarter-finals. 

Claudio Ranieri's men hadn't triumphed at Highbury since November 1998, but their 2-1 victory was a sign of things to come – namely a blue tidal wave of Roman Abramovich's petrodollars which engulfed Arsenal over the next few years. 

This game demonstrated that for all their domestic excellence, Arsenal circa 2004 were a busted flush in Europe. More long-term, it symbolised a monumental power shift in English football, one from which the Gunners have still never recovered.

5. The windfall final: Arsenal 0-0 Man United, May 2005

Intent on seeking revenge for the 2-0 October 2004 loss at Old Trafford which ended Arsenal's 49-match unbeaten run in the league, the capital club took on their deadly rivals in the 2005 FA Cup Final without injured talisman Thierry Henry.

United dominated but in a very un-Arsenal-like performance under Wenger, the Frenchman's side sat deep in behind Dennis Bergkamp in a 4-5-1, rode their luck and clung on for penalties. Patrick Vieira scored the decisive spot-kick to bring the FA Cup back to Highbury – his last kick in an Arsenal shirt – and the Gunners have never quite been the same since. 

4. Eight to be a Gooner: Man United 8-2 Arsenal, Aug 2011

Arsenal had already started the 2011-12 season badly, having drawn on the opening day at Newcastle and then lost to Liverpool on home turf. So what better way to worsen the mood than a horrifying thumping at one of your biggest rivals?

Arsenal were three down by 40 minutes and trailed 6-1 with 20 left on the clock, before Robin van Persie’s consolation was quickly drowned by further goals from Wayne Rooney and Ashley Young. Arsenal recovered to secure a third-place finish, but this was still a sour season.

3. Mind the age gap: Arsenal 1-3 Man United, May 2009

Arsenal players accused Manchester United’s Patrice Evra of showing a lack of respect after the Frenchman described the second leg of the 2009 Champions League semi-final at the Emirates as being like "11 men against 11 babies". 

But it was hard to disagree with the left-back’s assessment. With the Gunners trailing 1-0 from the first leg, a masterful Cristiano Ronaldo swept United into the final and condemned Arsenal to a 4-1 aggregate loss. 

The Gunners’ move to a new ground in 2006 was supposed to confirm their status as a European powerhouse, but this horrendous loss confirmed they were playing second fiddle.

2. “We won the league in…” Man United 0-1 Arsenal, May 2002

"It was men against boys," admitted Manchester United captain Roy Keane after seeing his team lose the game – and title – to Arsenal at Old Trafford in 2002. 

Wenger's side, suitably clad in gold, dictated the pace of the match early on before driving forward after the interval. Freddie Ljungberg's shot was parried by Fabien Barthez, and Sylvain Wiltord tucked home the rebound to bring the championship crown back to Highbury for the second time under Wenger. 

A point would have been enough for Arsenal, but Wenger urged his side to "win the title with a bang". They duly delivered.

1. A perfect day: Arsenal 4-0 Everton, May 1998

On a sun-drenched afternoon at Highbury, all the old Arsenal urban myths were laid to rest as the Gunners secured their first title under Wenger, hammering Everton thanks to a turbo-charged Marc Overmars display. 

In the dying minutes, Tony Adams controlled the ball with his chest and smashed home in front of the North Bank to make it 4-0 and win the league in front of his team’s own fans. 

Arsenal completed the domestic Double a week later. The defensive shackles had been removed, and taking into account the pyrotechnic nature of modern football, Wenger's fusion of Dutch/French guile and English grit meant the '98 vintage were arguably the greatest of all.