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 was hoped he could be like a new signing for the Reds in 2019/20. It's no mean feat recovering fully from such a terrible injury to take active part in Klopp's demanding style of play. Oxlade-Chamberlain featured regularly from the second part of the season, yet not guaranteed a starting place. He still managed to score eight goals in the historic 2019/20 season.

A knee injury kept Oxlade-Chamberlain out of action until December 2020. Only two of his thirteen league appearances were starts, but he then enjoyed the benefit of a full pre-season and was included in the starting eleven for the opening fixture of 2021/22 at Norwich. He featured regularly in the first half of the season but not so much after Christmas, finishing the season with three goals from 29 appearances. A hamstring injury meant Ox missed the first two months of 2022/23 and he started just four league games before leaving the club at the end of the season on expiry of his contract. On 14 August 2023 it was announced that Oxlade-Chamberlain had agreed a three-year deal with Turkish side Besiktas.

The move promised regular football, a chance to rediscover form, and a platform to showcase the qualities that once made him so influential in the Premier League. In his first campaign with Besiktas, Oxlade-Chamberlain featured in 30 games, scoring 4 goals and notching 1 assist across all competitions. While those figures offered encouraging flashes, injuries consistently disrupted his rhythm and availability. He had a three month spell on the sidelines with a torn thigh muscle. In the midst of the 2024/25-season, under caretaker and eventually permanent manager Ole Gunnar Solskjær, Ox experienced a revival. After being given a chance as a substitute in early December, he scored the only goal in a 1-0 win over Fenerbahce in just his second outing that season. That performance earned him greater trust and he went on to start practically every league game following the January 2025 managerial change. Unfortunately, that run was cut short by a knee injury in the spring, dampening the momentum he had rebuilt.

In total, Oxlade-Chamberlain played 50 matches for Besiktas across all competitions, scoring five goals. He also collected silverware, helping the club to win both the Turkish Cup and the Super Cup. Yet with fitness concerns persisting, his contract was ended by mutual agreement in July 2025, a year before it was due to expire. His time in Istanbul was therefore a familiar mix of bright moments, substitute cameos, and frustrating spells in the treatment room. Supporters recognised his commitment and quality when fit, but ultimately his Besiktas chapter ended in the same way as several others in his career - with glimpses of what he could offer, but limited by injuries.