This research is focused on the monitoring and diagnostic of the bottoming cycle (BC) of a large size combined cycle, composed by a three pressure level HRSG (Heat Recovery Steam Generator), a three expansion level steam turbine and auxiliary pumps. An original Matlab software was developed, which is composed by two parts: the first calculates HRSG performance, while the second is focused on the calculation of the steam turbines performance, at different power plant operating conditions. In the first part a complete HRSG performance analysis is carried out: it consists of the calculation of each heat exchanger performance and health. The direct result of this analysis is the definition of Non Dimensional Performance Indexes (NDPI) for each heat exchanger, which define the instant degradation of each component, through the comparison between the “actual” and the “expected” effectiveness. The second part calculates steam turbines performance. Two NDPIs are defined: one referred to the high pressure steam turbine and the other referred to the middle-low pressure steam turbine. The performance indexes are calculated comparing the actual expansion efficiency with the expected one. The NDPI previously defined will be used to monitor plant degradation, to support plant maintenance, and to assist on-line troubleshooting. Each performance parameter is coupled with an accuracy factor, which allows to determine the best parameters to be monitored and to define the related tolerance due to measurement errors. The methodology developed has been successfully applied to historical logged data (2 years) of an existing large size (400 MW) combined cycle, demonstrating the capabilities in estimating the degradation of the BC performance throughout plant life.