In the period 2001 to 2003, the New South Wales legislature enacted four Acts that impinge on the assessment of damages in litigation against health professionals. They are the Health Care Liability Act 2001 (NSW), the Civil Liability Act 2002 (NSW) (as originally enacted), the Civil Liability Amendment (Personal Responsibility) Act 2002 (NSW) and the Civil Liability Amendment Act 2003 (NSW). This article considers the principles on which damages are assessed in medical litigation and how those principles have been affected by these four enactments. It points out that each piece of legislation was retrospective in applying to events that occurred both before and after its commencement. However, proceedings already issued before a particular date were excluded in each case from the retrospective operation of the legislation. The article provides details of the relevant dates of operation of each of the statutes.