M.Com. (SA & International Taxation ) / Players’ contracts in sports are assets for the professional clubs. Like any other assets, these contracts could be sold to other clubs, locally or internationally, at a fee. The South African Revenue Service has issued a “Draft guide on the taxation of professional sports clubs and players” (hereafter the Guide). This Guide was issued as a draft in 2010 and had not been finalised at the time of the completion of this dissertation. Using a doctrinal research methodology, which includes a systematic exposition of the Guide by using the Income Tax Act 58 of 1962 (hereafter the Act), case law and the other appropriate literature, this study is aimed at interpretatively reviewing the contents of this Guide, specifically the section of the Guide that deals with the income tax implications arising from the transfer of players. The review of the Guide revealed that the Guide is technically incorrect in certain aspects. For instance, the definition of “asset” per the Eighth Schedule of the Act was incorrectly cited to specifically exclude trading stock. In addition, the Guide has excluded from its scope transactions between residents and non-resident clubs and players. Furthermore, the Guide did not deal with all aspects relating to player transfers, such as player swops and third party ownership of player rights. In some instances, the Guide was found to be ambiguous, especially in dealing with free transfers. The study has found that the transfer fees could either be included in gross income or be subject to capital gains tax for the transferor club, depending on whether their nature was revenue or capital. The deciding factor was determined to be the intention of the transferor club at the time of transfer of the player rights. Where the intention of a transferor club is to enter into a profit-making scheme, the transfer fees would be revenue in nature and included in gross income in terms of s 1 of the Act (Elandsheuwel Farming (Edms) Bpk v SBI, 39 SATC 163). Where the intention of a transferor club is to use the player as income-producing asset, then the transfer fees would be capital in nature, and be subject to capital gains tax. For the transferee club, it was determined that the player is usually acquired to bring to the club an advantage of the enduring benefit (British Insulated and Helsby Cables v Atherton 1926 A.C. 205). This therefore implies that the transferee club would not be able to claim the deduction under s 11(a) of the Act. The study will be useful to the sports clubs as it provides a comprehensive guide on the income tax treatment of player transfers.