#1 Alfredo di Stefano to Real Madrid (1953-64)

Transfer Fee: £195,000
Major Honours: 15 (1x Intercontinental Title, 5x European Cups, 8x League Titles, 1x Spanish Cup)
It should come as no surprise that the most successful European club of all time has achieved the three most successful transfers of all time.
Two time Ballon d'Or winner, di Stefano had achieved most of his Real Madrid success prior to the individual award existing. Signed for a modest £195,000 in today's money from Argentinian side, River Plate, di Stefano inspired the greatest Real Madrid side in history to unprecedented success.
They won five consecutive European Cups between 1956 and 1960, largely due to the goal-scoring prowess of the Argentinian striker.
Unlike the current Madrid team, their 1950's counterparts were just as successful domestically as they were in Europe and di Stefano inspired them to an incredible eight La Liga successes.
The prolific Argentinian scored 156 goals in 232 matches - a very healthy return on a £195,000 transfer fee. Undoubtedly, the most successful transfer of all time.