Born in Portsmouth in 1993, Oxlade-Chamberlain joined Southampton's academy aged seven, making his Saints debut aged sixteen in March 2010 as a substitute in a League One fixture against Huddersfield. The following season he scored nine goals as Southampton were promoted and in August 2011 he signed for Arsenal for an initial fee of £12million. In his first season in the Premier League, he was nominated for PFA young player of the year award and was called up to England's Euro 2012 squad.

Over six seasons Oxlade-Chamberlain scored 20 goals for Arsenal in 198 appearances but with a year left on his contract stated a desire to leave in the summer of 2017. He looked set to move to Chelsea but turned it down despite the clubs agreeing on a fee. He then joined Liverpool in a £35 million deal a few days before the end of the transfer window, his last appearance for Arsenal having ironically been in a 4-0 defeat against Liverpool at Anfield.

Oxlade-Chamberlain had to be patient and wait for opportunities, but by the spring of 2018, he had become an integral part of Liverpool's midfield. His season came to an end though when he suffered multiple knee ligament damage making a tackle in the first leg of the Champions League semi-final with Roma. During the close season, the full extent of the injury was revealed when Jürgen Klopp announced that it was likely to rule him out for all of the 2018/19 season, with the focus being on rehabilitation.

The recovery was slightly quicker than expected and Oxlade-Chamberlain made his first appearance for the Under 23's on 8 March 2019. A slight hamstring injury slowed his progress but he did receive a huge ovation when he came off the bench with seventeen minutes remaining against Huddersfield in the penultimate home game. A further brief substitute appearance against Wolves on the final day followed and he was on the bench for the Champions League final. With a full pre-season behind him, it is hoped he can be like a new signing for the Reds in 2019/20.