This article was first published in September 2016 and has been updated.
After a fourth defeat in a row in all competitions, Arsene Wenger's tenure at Arsenal looks set to end. While he has obviously had some of the best moments in the club's history, here are his 10 worst.
10. 2001 FA Cup final
It was a game Arsenal largely dominated and were leading with just seven minutes to go. This was Wenger's second great Arsenal team in development, moving on from the double winners of 1998 and toward those of 2002, but they could have collected a trophy during that transition.
After being the better team against Liverpool, they finally took the lead in the 72nd minute, with Freddie Ljungberg rounding Sander Westerveld to score. And all looked well, until 10 minutes later, when Michael Owen firstly popped up to snaffle an equaliser, then outpaced Tony Adams to flick home a winner with extra time looming.
"It was obvious that we should have won, and we had a clear penalty turned down," Wenger said afterward, "but this the story of our season."
9. 10-2 on aggregate vs. Bayern Munich in 2017
Wenger's latter-years at Arsenal have suffered some grim European capitulations, from what seemed like the annual defeat to Barcelona, to the 2015 loss to Monaco -- they've all been dispiriting in their own way.
But the 10-2 aggregate humiliation by Bayern Munich last season surely topped them all. Being beaten -- outclassed, even -- by Bayern isn't necessarily embarrassing, but the manner of their capitulation was. At the end of the second leg, at the Emirates, the home fans could barely even bring themselves to boo.
8. Players moving on to greater success
As the 2000s turned into the 2010s, Arsenal's lack of a tangible success was bad enough. But perhaps worse was the steady exodus of their best players for bigger, richer, more-successful destinations.
Kolo Toure, Samir Nasri and Gael Clichy won the league with Manchester City, Cesc Fabregas lifted six trophies with Barcelona and perhaps most hurtfully of all, Robin van Persie virtually won the Premier League for Manchester United on his own. It only served to emphasise that Arsenal didn't want for talent, rather they firstly couldn't hold onto that talent -- and perhaps that quality in their ranks wasn't their fundamental problem.
7. 1999 FA Cup semifinal, trip to Leeds
The 1998-99 season is remembered as Manchester United's great work, a remarkable and never-to-be-topped Treble. But actually, Arsenal came pretty close to ruining it all for Ferguson's men, in two competitions.
Firstly, the FA Cup, where United won the semifinal thanks to that Ryan Giggs goal, but it could so easily have been Arsenal's, as Peter Schmeichel saved a penalty from Dennis Bergkamp. And then the league: People forget that United only actually won the league by a single point, and Arsenal topped the table with two games to go, having gone undefeated since mid-December. However, they travelled to Leeds on a Wednesday night in May and lost 1-0, thanks to a late Jimmy Floyd Hasselbaink header. United's draw with Blackburn then a win over Tottenham were enough for the title.
6. 2000 UEFA Cup final
The biggest hole in Wenger's record is a lack of a European trophy, despite competing on the continent every year. Perhaps his best chance of winning one came in 2000, when after departing the Champions League -- with the decision to play group games at Wembley backfiring -- they sashayed through to the UEFA Cup final, where they would play Galatasaray in Copenhagen.
After a scoreless 120 minutes, when neither side could claim a golden goal, the match was decided on penalties, which couldn't really have gone much worse for Wenger's side. Davor Suker and Patrick Vieira missed, the latter hammering his effort against the bar, while the Turks slotted away four in a row and lifted the trophy.
5. 2009 Champions League semifinal
Whether, ultimately, it would have mattered is a point for debate. Manchester United came up against Pep Guardiola's great Barcelona in the final and never looked like winning, so neither would Arsenal, one could imagine, had they made it through. But this was still a sickener, particularly after only losing 1-0 in the first leg of the semifinal at Old Trafford, theoretically setting up the Gunners promisingly for the return. Instead, they were pulled apart, with goals from Cristiano Ronaldo and Park Ji-Sung killing off the tie after just 11 minutes, then another from Ronaldo on a brilliant and exhilarating counterattack drove the point home further.
4. Staying on too long?
Not a moment per se, but Wenger shouldn't still be there. Few will doubt that his achievements have been extraordinary, that he has revolutionised a club and possibly English football and that to keep a club like Arsenal at the level he has, with the resources available, is remarkable. But he should have realised he has taken Arsenal as far as he can long ago, that by now someone else with fresh ideas should come in and move them on. Only Wenger will decide when he leaves Arsenal, but the most he can hope for at this point is that the last few years haven't tarnished the memory of the good times too much.
3. 2006 Champions League final
Ah, what could've been. One could perhaps forgive Arsenal for losing the 2006 Champions League final to the first great Barcelona team of this generation, featuring Andres Iniesta, Ronaldinho and Samuel Eto'o. And yet, it could all have been very different.
Jens Lehmann was sent off for a reckless lunge on Eto'o after just 18 minutes, but despite their numerical disadvantage, Arsenal not only took the lead, through a Sol Campbell header, but they held it until the 76th minute. Alas, then Eto'o and, of all people, Juliano Belletti scored, and Barca had the trophy. Blame Lehmann. Blame the anonymity of Thierry Henry. Blame Wenger's tactics: He hasn't come as close to the top prize since.
2. 2011 League Cup final
After six barren years, with no trophy while most of Arsenal's major rivals collected honours of various kinds, this was to be something, at least. The League Cup is comfortably fourth in any big club's list of priorities, but it would be a major trophy, something to cling to. And after the Gunners reached the final in 2011, where they would face a Birmingham side heading for relegation, it seemed as if all they had to do was turn up and not do anything stupid, and the cup would be theirs.
They managed the first bit, but alas, the second eluded them. Nikola Zigic's opener was cancelled out by Robin van Persie, but with a minute to go, Laurent Koscielny and Wojciech Szczesny briefly departed reality, allowing Obafemi Martins to tap in the winner. Even a consolation prize disappeared down the lavatory.
1. Manchester United 8-2 Arsenal
You know a defeat is really bad when the opposition starts to feel sorry for you. Sir Alex Ferguson was not a man to readily dish out sympathy to opponents, but as his team ran in goal after goal in this league game in 2011, he admitted that he wanted the scoring to stop, to not humiliate a team and a man that used to be his equal.
The Arsenal lineup was a calamity, featuring Johan Djourou, Armand Traore and Francis Coquelin (before he was good), but even so, to be so thoroughly beaten was a tragic embarrassment. Trudging off, Wenger looked like a man who didn't know what to do.
"Of course you feel humiliated when you concede eight goals," he said. "It was a terrible day."