After a review of the evaluation of urban regeneration initiatives from 1968 to 1997, and a discussion of the development of output and performance measures that underpinned the monitoring of regeneration initiatives, this chapter examines how monitoring and evaluation are put into practice, using City Challenge as an example. The City Challenge initiative provided the foundation for monitoring and evaluation of subsequent regeneration initiatives, including the Single Regeneration Budget Challenge Fund and New Deal for Communities. The format of monitoring, the list of core outputs, the definitions of outputs and the arrangements for local and national evaluation of subsequent initiatives, all originated from the practice of City Challenge (see the guidance notes for Single Regeneration Budget Schemes and New Deal for Communities, in particular those on monitoring and evaluation). The practice of continued grant payment being dependent on satisfactory scheme delivery, and the arrangements for mid-year and annual reviews were important features in the management of City Challenge programmes. Hence, a study of the completed City Challenge initiative provides a useful framework to understand the actual implementation of monitoring and evaluation at the local level.