Professional football contracts were established in England in 1885 and structured around a transfer and retain system whereby at the end of the contract clubs decided whether to retain or transfer the player. These contracts also had a maximum wage value so it is fair to say clubs were firmly in control of players’ careers and earning capacities. However the early 1960s altered such labour conditions as the maximum wage was abolished (in 1961) whilst the retain and transfer system was overhauled as a case of unreasonable restraint of trade (in 1963). Contractual freedom and better earning conditions were further enhanced in 1978 when the Independent Tribunal System was established to deal with out-of-contract professional players who sought to move to a new club having declined a retaining contract from their current club. The 1995 Bosman Case further lubricated the marketplace as players were now provided with total contractual freedom for the first time. This paper assesses contract power over professional football’s historical timeline and demonstrates that the professional football marketplace has seen the pendulum of power swing away from the football authorities toward the player with regard to professional contracts.