This thesis considers certain consequences following contractual failure in South African and Scots law in comparative perspective. Three species of contractual failure are under review: termination after breach; termination after supervening impossibility/frustration; and termination of a contract which is voidable by reason of improperly obtained consent. The focus is on the following: (a) the legal effect of termination for breach on the contractual nexus between the parties; (b) the claim which allows a party to enforce a right to a contractual performance after contractual failure; (c) the claim for the return of a contractual performance (or the value thereof) conferred prior to termination for breach; (d) the claim designed to redress the economic imbalances between the parties after supervening impossibility of performance/frustration; and (e)the claims designed to redress the economic imbalances between the parties after termination of a contract rendered voidable by reason of improperly obtained consent. The central argument is that in choosing between defensible doctrinal alternatives to regulate the consequences of contractual failure, a legal system must not rely exclusively on abstract taxonomic arguments, historical arguments or comparative arguments. I argue that this choice should be made after careful consideration of the principles of recovery underpinning a particular remedy and the consequences of imposing liability according to a particular doctrinal set of rules. The proper doctrinal basis of a particular remedy is the one which, having due regard to the consequences of imposing liability according to a doctrinal set of rules, most accurately reflects these principles of recovery.