The 24-year-old has won three FA Cups since joining the Gunners from Southampton in 2011 but believes a move is necessary for his development and quest for major silverware.
Premier League champions Chelsea agreed a £35million transfer fee for the England international but his next destination remains unclear as he is said to favour a move to Liverpool.
But whether he chooses Stamford Bridge or Anfield as his next home, the recent developments over his future have come as a significant shock for Arsenal fans.
While the versatile star has rejected multiple contract offers at the Emirates, many Gooners felt he would stay put and eventually put pen to paper, particularly given the fact that Arsene Wenger has publically suggested he will not be sold.
So what has the Arsenal manager actually said about Oxlade-Chamberlain over the last five months and how has his stance changed so drastically?
March 8 – Dismissing reports he wants to leave:
I haven’t seen that, I don’t know. All I can say is personally I rate him highly, I showed that in the way I kept faith in him when he was injured.
I personally wish that he stays at the club, he’s a very promising player who has developed very well, looks to have the values we rate at this club.
April 10 – Wenger sends clear message to Arsenal:
I personally think it is vital that Chamberlain stays at Arsenal. We bought him when he was very young, we have built him up and I think he has a great mentality.
I like his mentality and he has a good football brain. It would be a big damage for us to lose this kind of player.
April 23 – Turning on his agent?
I want Oxlade-Chamberlain to be part of Arsenal Football Club for the next ten years.
He is a big player and we live in a world where agents are linked to the press and can always have a tactic to make the whole package come up.
But at the end of the day it all comes down to “do you want to be part of that?
Do you meet your needs and what is important in your football life here or not?”
April 26 – Beginning to lose hope over a contract extension?
It will be decided in the summer – we have a big job to do in the summer.
May 4 – Wenger sends direct message to the player:
He looks like he’s made a move forward, I’m pleased with him.
I believe that he’s happy in his new position – at the moment he’s convinced that he has all the qualities to play there and it’s given him confidence.
He has to commit his future to the club and hopefully he’ll do so in the summer.
July 15 – Oxlade-Chamberlain will ‘100% stay’:
I expect him to stay, 100%. No matter the speculation, he will stay.
August 9 – The Ox tipped to become ‘very great player’ at Arsenal:
He’s had some small injuries but last year he was much more stable. I think he is a hugely talented player who is on the way up.
He will continue to move up because the potential is there. Personally I believe he will be a very great player.
August 16 – best of his generation?
I want him to stay here for a long time – I’m convinced that he will be in the next two or three years the English player everyone looks at.