The worsening with age of technical systems performance is a matter of fact which is particularly timely to analyze for horizontal-axis wind turbines because they constitute a mature technology. On these grounds, the present study deals with the assessment of wind turbine performance decline with age. The selected test case is a Vestas V52 wind turbine, installed in 2005 at the Dundalk Institute of Technology campus in Ireland. Operation data from 2008 to 2019 have been used for this study. The general idea is analyzing the appropriate operation curves for each working region of the wind turbine: in Region 2 (wind speed between 5 and 9 m/s), the generator speed–power curve is studied, because the wind turbine operates at fixed pitch. In Region 2 12 (wind speed between 9 and 13 m/s), the generator speed is rated and the pitch control is relevant: therefore, the pitch angle–power curve is analyzed. Using a support vector regression for the operation curves of interest, it is observed that in Region 2, a progressive degradation occurs as regards the power extracted for given generator speed, and after ten years (from 2008 to 2018), the average production has diminished of the order of 8%. In Region 2 12, the performance decline with age is less regular and, after ten years of operation, the performance has diminished averagely of the 1.3%. The gearbox of the test case wind turbine was substituted with a brand new one at the end of 2018, and it results that the performance in Region 2 12 has considerably improved after the gearbox replacement (+3% in 2019 with respect to 2018, +1.7% with respect to 2008), while in Region 2, an improvement is observed (+1.9% in 2019 with respect to 2018) which does not compensate the ten-year period decline (−6.5% in 2019 with respect to 2008). Therefore, the lesson is that for the test case wind turbine, the generator aging impacts remarkably on the power production in Region 2, while in Region 2 12, the impact of the gearbox aging dominates over the generator aging; for this reason, wind turbine refurbishment or component replacement should be carefully considered on the grounds of the wind intensity distribution onsite.