The Income Tax Act 58 of 1962 (“Act”) entitles taxpayers to deduct certain losses and expenses incurred by them from their taxable income if such losses and expenses comply with the requirements of section 11(a) of the Act. One of the requirements of section 11(a) is that, in order to be eligible for a deduction, the losses and expenses must have been “actually incurred” by the taxpayer. The area of tax deductions in our tax law represents the frontline in the continuous and inevitable war between the taxpayer (almost always desperately trying to maximise her deductions) and the revenue authorities (as often times desperately trying to minimise the deductions to which the taxpayer is entitled). The stage on which the various battles which make up this mighty war between citizen and state are fought is the court and the arsenal with which each party comes armed is the Act and, more specifically, the absolute belief of each party in the correctness of their interpretation of the Act, which, each party hopes, will be ably demonstrated by their able (and often extremely expensive) counsel. Such is the determination of the taxpayer and the tax authorities alike that the body of case law relating to this specific area of our law is, especially when one considers that it essentially involves on only one section of the Act, relatively voluminous. The author’s intention is to consider only one of the requirements with which the taxpayer must comply in order to be eligible for a deduction, namely, the requirement that the relevant loss or expenditure must have been “actually incurred” by the taxpayer. Despite the fact that the meaning of the phrase “actually incurred” has been considered extensively by our courts, significant uncertainty still exists as to its exact meaning. The author will deal with three specific contexts in which the meaning of this phrase remains a subject of uncertainty, namely, share-based payments, contingent liabilities and losses and expenses incurred in relation to illegal receipts. The author will begin first by dealing with the interpretation of tax statutes, the author will then, in general terms, consider the general deduction formula after which the author will delve into the meaning of the phrase “actually incurred” in the contexts of each of the transactions mentioned above. / Dissertation (LLM)--University of Pretoria, 2012. / gm2014 / Mercantile Law / unrestricted