Dynamic decision-making processes in the football transfer market, intense rivalry for top talents, and rapid development of communication technologies enable clubs and players to negotiate simultaneously with many entities. Although these phenomena may, sometimes, seem beneficial to the actors of a football market, they also can create some serious legal problems. Football clubs withdraw from transferring a player, in favour of another prospective signing, even at some very late stage of negotiations. Similarly, football players negotiate with clubs, and sign preliminary agreements, but then refuse to conclude a final contract. Confusion and uncertainty about the legal situation are increased by differences between legal cultures that are represented by different football stakeholders. This article aims to discuss the practical aspects of unfinished football transactions. It attempts to define the criteria of finalisation of professional football contracts and international transfer agreements. It also presents arguments for claims regarding breaches of pre-contractual and contractual obligations of football stakeholders. In this article, it is argued that the jurisprudence of football judicial and arbitration bodies distinguishes between preliminary agreements, draft contracts, and final contracts. They set clear principles regarding the calculation of compensation for breaching pre-contractual and contractual obligations. They also offer a legal basis for claims based on negligent, unfair, or disloyal negotiating, although these are still very rare in football dispute resolution.