6. Arsenal 2-1 League Cup defeat to Birmingham

2011 was certainly not a good year for Arsenal. It is the same year they lost 8-2 to Manchester United at Old Trafford but earlier that year in February, even a bigger blow had torn the Gunners camp apart.

League Cup final at Wembley Stadium, Arsenal as you would expect were the favorites against relegation-threatened Birmingham City. The underdogs scored first through Zigic but Robin Van Persie levels it.

In the last seconds of the match, when everybody expected extra-time Gunners win, a calamitous mix up between young goalkeeper Wojciech Szczesny and defender Laurent Koscielny gave Rubin Kazan loanee Obafemi Martins an opportunity to win his team the first ever trophy since 1963. Am sure you are yet to come across a Gooner who likes this story.

5. Gerrard slip against Chelsea

This might not be a record as such but the result of that slip is what will haunt Liverpool as a club and one man in particular in the name of Steven Gerrard for decades.

The match against Chelsea came in 2014 when the Reds were looking like title favorites. Brendan Rogers Suarez inspired side had gone for 11 matches unbeaten and so it was one more win and the title was within reach. Then this happened, at the end of the first half, Gerrard slipped while receiving a pass and Demba Ba took full advantage. He scored for the Blues and the Reds never got back in the game.

Willian scored the second later in the game and the title was gone. Manchester City won their game in hand later and Etihad celebrated their second league crown in five years. Gerrard has won all titles available in club level including the Champions League but the league is a bad miss for him. If the Reds win the League this season, he will be over the moon.

4. Manchester United 6-1 defeat to rivals City

In 2011, a few months after destroying Arsenal 8-2 at Old Trafford, Manchester United suffered what Sir Alex called his worst ever defeat both as a player and Coach. To make matters worse the 6-1 lose came in the hands of bitter rivals and cross-town side Manchester City.

“It was our worst ever day,” Ferguson said.

“It’s the worst result in my history, ever. Even as a player I don’t think I ever lost 6-1. I can’t believe the scoreline. The first goal was a blow for sure, but it was retrievable at 1-0.

“I’m shattered, I can’t believe it. It was an incredible disappointment, but we will react, no question about that. It’s a perfect result for us to react to because there is a lot of embarrassment in the dressing room — and quite rightly so — and that will make an impact. You have to recover. The history of Manchester United is ‘another day’ and we will recover.” Fergie remarked.

3.Chelsea- Worst Premier League Champions of All-Time

Chelsea became the worst Premier League Champions of all-time in 2015/16 after finishing 10th in the league, 1 year after lifting the title under Jose Mourinho. They started the season badly under the ‘Special One’ but things go out of hand and he was sacked.

Guus Hiddink was brought in to steer the ship for the remaining six months but the damage was already done. They ended up in the 10th place with 50 points and 12 defeats. Blackburn Rovers ((1995/1996) and Manchester United (2013/2014) had terrible campaigns but they both managed a 7th place finish.

2. Arsenal humiliating 8-2 defeat to Man United

Arsenal fans have enjoyed matches against Manchester United over the years but on this day in 2011, they certainly did not enjoy a thing. The Gunners came to Old Trafford expecting to get their fans back in the mood after losing their Captain Cesc Fabregas to Barcelona and key player Samir Nasri to Manchester City.

The whole drama turned from bad to worse, Red Devils did not expect such a depleted side at Old Trafford and so they just started tearing the visitors apart. The Gunners had no answers and so the demolition continued. Van Persie and Walcott tried to minimize the damage but when it got to 7 then 8 and nobody could cover the volcano anymore. If you watched the match, you will remember well that the score could have been worse if the hosts scored ¾ of their chances. It was that bad and nobody at Emirates or around the World want to be reminded about this day.

1. AC Milan lose to Liverpool in 2005

Champions League is a competition that any serious football fan cannot afford to miss. It gets even better when the competition gets to knockout stages, quarters, semis and the final. All the stars from all corners of the globe fight it out every year for the coveted European club crown.

In the last two decades, records have been set and others broken but there is one that will remain intact for many years to come and that is Istanbul final in 2005. The game was between giants AC Milan and four times winners Liverpool.

The Italians scored 3 goals in the first half through Maldini and Crespo and some fans even went to bed because the match seemed dead and buried. However, Rafa Benitez hatched a plan at halftime and in the second half they destroyed Milan in six minutes to make it 3-3 and push the match to extra-time and then penalties. The Reds won the trophy thanks to heroics of Jerzy Dudek.

Brazilian star Kaka still feels pain about the lose 11 years later. He recently told a local radio exactly how he felt.

“Honestly, years later I still can’t understand how we managed to lose that game. We had the best defenders in the world in that team,’’ Kaka said.

“Our back four was Cafu, Jaap Stam, Alessandro Nesta, and Paolo Maldini but we still let in three goals in six minutes. Something amazing happened that can’t be explained.

“All you can really say is that in football these things can happen. Especially in the Champions League, we have seen truly incredible things happen.”