Wayne Rooney: £27million, Everton to Manchester United (2004)
Already an England international, and one of the hottest properties in European football after a blistering Euro 2004, Rooney became the most expensive British teenager in footballing history when he left Everton for a cool £27m. Barring a rotten World Cup and a loss of form that lasted the best part of a year, it's gone relatively well for Rooney at Old Trafford with four Premier League titles (thanks in part to over 100 PL goals from Rooney), the Champions League and a couple of League Cups.
Theo Walcott: £12million, Southampton to Arsenal (2006)
Sven-Goran Eriksson shocked the footballing world by naming the 17-year-old in his 2006 World Cup squad, just five months after Arsenal signed him from Championship side Southampton and before he had even made his Gunners' debut. Four years later he wasn't even in Fabio Capello's 2010 squad after four years in which his blistering pace had often been followed by infuriatingly mindless footballing decisions. Has he been worth the money? Over five years on and the jury is still out.
Gareth Bale: £10million (including add-ons), Southampton to Tottenham (2007)
It's fair to say that Bale struggled in his first two years at Spurs, as the north London side failed to win any of the first 24 Premier League games he started. Bale was so underwhelming that boss Harry Redknapp was ready to send him on loan in January 2010 until he accidentally discovered that he was rather a good left-winger. A Champions League hat-trick against Inter at the San Siro later and he's the reigning PFA Players' Player of the Year and apparently worth around £50m.
Fabian Delph: £8million, Leeds to Aston Villa (2009)
Remember him? Delph was one of the Football League's brightest prospects when, still only 19, he completed a big-money move to Villa. Competition for places and long-term injuries have limited Delph to just eight Premier League starts in his first two seasons at Villa Park, but he efforts were rewarded with a new long-term contract in March 2011. He still has rather a long way to go to justify that transfer fee.
Glen Johnson: £6million, West Ham to Chelsea (2003)
Johnson was the first signing of the Roman Abramovich revolution at Stamford Bridge in 2003. Then 18 - and with just a handful of first-team appearances under his belt - he found first-team football hard to come by under both Claudio Ranieri and Jose Mourinho, moving to Portsmouth in 2006. Some fine performances at right-back for the south-coast club earned him a second big-money move, in 2009, this time to Liverpool (for a fee in the region of £17.5million). Worryingly, he now has 34 England caps despite not being a terribly good defender.