Wind turbine power upgrades have recently become a debated topic in wind energy research. Their assessment poses some challenges and calls for devoted techniques: some reasons are the stochastic nature of the wind and the multivariate dependency of wind turbine power. In this work, two test cases were studied. The former is the yaw management optimization on a 2 MW wind turbine; the latter is a comprehensive control upgrade (pitch, yaw, and cut-out) for 850 kW wind turbines. The upgrade impact was estimated by analyzing the difference between the post-upgrade power and a data-driven simulation of the power if the upgrade did not take place. Therefore, a reliable model for the pre-upgrade power of the wind turbines of interest was needed and, in this work, a principal component regression was employed. The yaw control optimization was shown to provide a 1.3% of production improvement and the control re-powering provided 2.5%. Another qualifying point was that, for the 850 kW wind turbine re-powering, the data quality was sufficient for an upgrade estimate based on power curve analysis and a good agreement with the model result was obtained. Summarizing, evidence of the profitability of wind turbine power upgrades was collected and data-driven methods were elaborated for power upgrade assessment and, in general, for wind turbine performance control and monitoring.