Arsenal's 10 Worst Moments Under Arsene Wenger

1-1999 FA Cup Semifinal

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Arsene Wenger led Arsenal to the double in 1998, and the following season they looked destined to repeat that feat. It was all going to plan until a last-minute penalty miss by Arsenal legend Denis Bergkamp in the FA Cup semifinal against Manchester United. The game went to extra time, and it was eventually won by a wonder goal by Ryan Giggs for United.
He seemed to beat almost half of the Arsenal team in a mazy run before finishing into the roof of the net past a hapless David Seaman. The goal was enough to give 10-man United the victory, and they went on to win not only the FA Cup but the Premier League and the Champions League too. It was a season of absolute glory for United, but if that penalty had gone in things probably would have been so different.
The goal by Giggs is still replayed to this day, and it still hurts as an Arsenal fan to see it 12 years later.

2-Leeds 1-0 Arsenal, May 1999

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Arsenal had lost their hold on the FA Cup only a few weeks earlier when a stunning Ryan Giggs goal helped United to beat them in the FA Cup semifinal. They were still favourites to lift the Premier League title though, and with two games left they were on top of the table. They travelled to Leeds United on a midweek night knowing that a win would put them in the driving seat, but their hopes were in tatters by the end of the match.
Nigel Winterburn had to go off injured with only 10 minutes left, and he was replaced by Nelson Vivas in the Arsenal defence. With only a few minutes remaining, Vivas failed to pick up Jimmy Floyd Hasslebaink at the far post, and the Leeds centre forward scored the goal to break Arsenal hearts. Only a few weeks earlier Arsenal had seemed destined for yet another double, but they ended the season without a trophy.
Arsenal won their final game against Aston Villa, but United beat Tottenham Hotspur on the same day to set up their most glorious season ever. It was a season of what might have been for Arsenal, and they had to wait another three years before they won another trophy.

3-2000 UEFA Cup Final vs. Galatasaray

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Arsenal had fallen behind Manchester United on the domestic front by the end of the 1999/2000 season, but they had a chance for glory in the UEFA Cup final against Turkish side Galatasary. Arsenal were favourites going into the game, but it was a fairly even contest up until extra time. With no goals in 90 minutes the game went into an extra half hour, with penalties to follow if the teams couldn't be separated.
Early in the first period of extra time, the pendulum swung in Arsenal's favour when Galatasaray's Gheorghe Hagi was sent off. He was their star player, and Arsenal took the chance to pour forward in search of a winner. Their attempts were in vain as they missed chance after chance, and the game went to penalties.
In the penalty shootout, Galatasaray went first and scored each of their first three penalties. Davor Suker missed Arsenal's first effort before Ray Parlour scored, but when Patrick Vieira missed the third one their chances were all but gone. Galatasaray dispatched their fourth effort and Arsenal finished as the runners-up yet again.

4-2001 FA Cup Final vs. Liverpool

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Arsenal played Liverpool in the 2001 FA Cup final, as they tried to end a run of three years without a trophy. As the match progressed, Arsenal eventually took the lead through Freddie Ljungberg and they looked destined to win their third trophy under Wenger. It had been a controversial game at that stage, as twice Liverpool players had handled the ball to prevent Arsenal scoring.
As the game wore on and Arsenal missed chances, their fans hoped they wouldn't pay the price. However, two goals in the final 10 minutes from Michael Owen turned the tide in Liverpool's favour and Arsenal somehow lost a game they should have easily won. It was a bitter blow for them, but the team recovered from it very well and came storming back the next season to win the double yet again.

5-2006 Champions League Final vs. Barcelona

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Arsenal had a pretty poor season domestically in 2006, but they reached the final of the Champions League for the first and only time so far in the club's history. Their defensive record in reaching that final was quite fantastic, as a makeshift defence kept 10 clean sheets in a row. They had to play Barcelona in the final and it was always going to be a very tough game for them.
Early in the game Arsenal goalkeeper Jens Lehmann was sent off for taking down a Barcelona player outside the box and Robert Pires was withdrawn to enable Manuel Almunia to play in goal. Arsenal took the lead against the odds when Sol Campbell headed home a free kick before halftime, and the dream was still alive. In the second half, Thierry Henry had a great chance to kill the game off, but he missed from close range and the tide turned in Barcelona's favour.
Barcelona equalised with 15 minutes left, and then took the lead with 10 minutes to go. Arsenal had worked very hard to stay in the game, but the 10 men struggled to find a way back against a very good team. The game ended 2-1 to Barcelona and Arsenal fans could only imagine what might have been if Lehmann had stayed on, or if Henry had taken his golden opportunity.

6-2007 Carling Cup Final vs. Chelsea

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Arsenal had used a mixture of fringe players, young players and more experienced players throughout their Carling Cup campaign in 2006/07. It was a policy which was continued in the final as Armand Traore, Justin Hoyte, Denilson, Jeremie Aliadiere and Julio Baptista all started the game. Arsenal took an early lead through a very young Theo Walcott, but the lead was soon cancelled out by Chelsea's Didier Drogba.
Drogba struck again for Chelsea with only six minutes remaining, and Arsenal were unable to find a way back in the 13 added minutes played. The game continued for such a long time firstly because Abou Diaby had knocked John Terry out with a kick to the face while clearing the ball, and then because of a mass brawl in added time. Three players were sent off after the brawl, and Arsenal finished the game with nine players on the field.
It was a game where Drogba yet again proved to be the scourge of Arsenal, and Philippe Senderos in particular. Despite a very good performance from an inexperienced side, they just didn't have enough on the day to meet the power of Chelsea.

7-Birmingham City 2-2 Arsenal, February 2008

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Arsenal had sold Thierry Henry to Barcelona in the summer of 2007, and they appeared destined to fall behind in the battle for trophies in England. However, they more than held their own in that season, and headed the table when they paid a visit to Birmingham City on Saturday, February 23rd. Arsenal started brightly, but after less than 10 minutes, the incident which ruined their season occurred.
Eduardo was crudely cut down by Birmingham's Martin Taylor, and the injury he suffered seemed to greatly affect the Arsenal players. It was an horrific injury from which he has not really fully recovered to this day, and he's a player who had such a bright future ahead of him at Arsenal. Birmingham took the lead, and Arsenal looked like it was all too much for them at that stage.
In the second half, Theo Walcott struck twice to put Arsenal ahead and it looked like the points would be theirs. They had a legitimate penalty claim turned down, and then in the final minute the referee gave Birmingham a penalty. Gael Clichy dithered when clearing the ball and he was almost robbed, but he managed to react just in time.
However, the referee saw things differently and Birmingham took their chance to grab a draw. Arsenal captain William Gallas lost the plot and threw a major sulk instead of trying to support his teammates. Arsenal's league season then fell apart, as they took only seven points from their next seven games.
That run included defeats to both Manchester United and Chelsea who were the only teams to finish above them that season. In the end, Arsenal put together a run of four wins in a row to finish the season, but they finished four points behind the eventual winners Manchester United. It was a season which could have ended so differently except for that fateful afternoon.

8-2009 Champions League Semifinal vs. Manchester United

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Arsenal had qualified for the Champions League semifinal in 2009, and when they drew Manchester United there was some real hope of another appearance in the final. Arsenal went to Old Trafford for the first leg and emerged with only a 1-0 defeat despite being completely outplayed. They needed to turn things around in the home leg, and to do so they had to be at their very best.
After only 11 minutes of the game at the Emirates, Arsenal's chances were in tatters, as United led 2-0 through goals from Ji-Sung Park and Cristiano Ronaldo. Arsenal again failed to turn up when it mattered most, but they eventually managed a late consolation from Robin van Persie after United had gone three up. Questions were asked of the Arsenal players' big-game temperament, and those questions are still being asked now two years later.

9-Tottenham Hotspur 2-1 Arsenal, April 2010

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Arsenal had not been beaten by their local rivals Spurs in over 10 years in the Premier League when the two teams met in April 2010. Arsenal were still just about challenging for the Premier League title, but they had to win to keep their chances alive. Arsenal had quite a few injury problems, but they still had a fairly strong team on the night.
Spurs scored an early goal when Manuel Almunia failed to deal with a long-range effort from Danny Rose, and Gareth Bale doubled their lead early in the second half. Arsenal suffered more injuries during the game, but when Robin van Persie was introduced midway through the second half the tide turned in their favour. Nicklas Bendtner pulled a goal back for them late on, but it was too little too late, and another season ended in disappointment.
The bragging rights for North London also disappeared that night, and Arsenal have not beaten Spurs in two league encounters since that game despite having a two-goal lead in each game.

10-2011 Carling Cup Final vs. Birmingham City

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Arsenal hadn't won a trophy in six years when they met Birmingham City in the 2011 Carling Cup final at the end of last February. They were clear favourites going into the game, as they were challenging for the Premier League title and Birmingham were fighting a battle against relegation. Arsenal had to do without the services of the injured Cesc Fabregas, but they still had enough quality players to win the game.
Birmingham took the lead after half an hour, but Robin van Persie equalised shortly before halftime. During the second half, Arsenal looked the most likely to grab a winner, but Ben Foster had his best game of the season in goal for Birmingham. Arsenal were a little shaky at the back, and in the very last minute, calamity struck.
Wojciech Szczesny came to collect a simple ball into the box, but Laurent Koscielny swung wildly at it and the ball fell to the feet of Obafemi Martins. He rolled it into an empty net and Birmingham saw out the last few minutes to claim a trophy for the first time in a very long time. It's impossible to tell whether Szczesny called for the ball or not, but if he did the mistake was all Koscielny's.
It didn't really matter whose fault it was though, as Arsenal had fallen at the final hurdle yet again.