Arsenal signed 17-year-old Alex Oxlade-Chamberlain from Southampton for an initial fee of £12million, rising to £15million on this day in 2011.
The latest star from the Saints academy after Gareth Bale and Theo Walcott had impressed during the 2010-11 season, scoring nine times as Nigel Adkins' men won promotion from Sky Bet League One.
It saw a number of clubs linked with the teenager but the lure of the club he supported as a boy and working under Arsene Wenger proved too strong for Oxlade-Chamberlain.
Having made his professional debut for Southampton at 16, he would not have to wait long for his bow in an Arsenal shirt but it proved a day to forget as the Gunners were thrashed 8-2 by Manchester United three weeks after he joined.
Oxlade-Chamberlain would quickly establish himself as a regular at the Emirates Stadium and played for England at Euro 2012 but injuries would soon trouble the midfielder and force him to miss the club's FA Cup triumph in 2014 and be restricted to a cameo role in their next FA final at Wembley a year later.
After seemingly shaking off his fitness concerns, the versatile ace would flourish at Arsenal during the following couple of seasons, playing a key role in their latest FA Cup success in 2017 before Liverpool came calling in August of that year.
Eventually Oxlade-Chamberlain, the son of ex-England international Mark, would move to Anfield for £35million but after a positive first campaign, a serious knee injury towards the end of the season prevented him from playing in the Champions League final or appearing at the 2018 World Cup.
Following 12 months on the sidelines, the midfielder would return but have to settle for an unused substitute role as the Reds claimed a sixth European crown with victory over Tottenham in Madrid in June 2019.
While injuries continue to plague the Portsmouth-born player, he helped Liverpool end their long wait for a Premier League title during the 2019-20 season but his subsequent fitness concerns have resulted in Oxlade-Chamberlain not playing for England in two years and also having to be content with a bit-part role under Jurgen Klopp.