6) Robbie Keane – £12m to Tottenham (rising to £16m with add-ons)
Keane lasted only 6 months at Liverpool following his £20m signing from Spurs, before he was sent packing down the motorway back to north London come the Christmas window. Because of our formation at the time with Fernando Torres leading the line, there simply wasn’t a role for the Irishman, who will now link up with Steven Gerrard again at LA Galaxy.
5) Andy Carroll – £15m to West Ham
We lost £20m on Carroll, but in fairness, we did brilliantly to get anywhere near £15m after our biggest ever transfer error: signing him for £35m. Since West Ham paid to keep the technically abject forward permanently, he’s scored seven Premier League goals in two injury hit seasons.