This thesis deals with the various ways taxpayers have employed to avoid paying tax on income, profits and gains and the responses of the judges and legislators. Each type of avoidance is followed from its first appearance to the present day, where appropriate. The respective manoeuvres of the taxpayers, on the one hand, and the Legislature, on the other, are chartered, as is the attitude of the courts. There are four sections. In the first, the various categories of tax avoidance arrangements that have been implemented over the years in the United Kingdom are examined. The second is concerned with international tax avoidance as seen from a United Kingdom perspective. Thirdly, the approach in the United Kingdom is compared with that of other countries, with particular reference to the United States of America, Canada and Australia. The last section analyses the role of the judges and examines the extent to which they have been prepared to look through the form of a transaction to consider the underlying substance. The role of the judges as makers of tax law is also considered. The way in which the subject was researched was to examine each category of tax avoidance in a chronological order, beginning with the first moves by the taxpayer, and charting the ensuing battle of wits between the taxpayer and the Legislature from the standpoint of those who have had to adjudicate on the process: the Judges.