Biomass continues to play a key role as an alternative to fossil fuels. Woody biomass produces lower greenhouse gas emissions than fossil fuels. However, in order to consider biomass as ‘green energy’, a number of factors should be taken into account, including the characterization of the quality of the resource. Therefore, monitoring quality parameters, such as moisture, ash, N content, is essential to assess the sustainability of biomass for energy production. This paper presents the results of laboratory analyses performed on wood chip samples from four Italian regions over a five-year period (2019–2023). In particular, all quality parameters defined by ISO 17225-9 for industrial wood chips were assessed. Data were analyzed using descriptive, parametric, non-parametric statistics, and multivariate analysis. An interest in quality monitoring has been observed, indicated by an increase in the number of samples received from suppliers and an enhancement in the average values of quality parameters. Moreover, an overall decrease in moisture and N content has been observed, while ash content and heating value have undergone non-linear variations. Statistically significant quality differences between samples from different regions may be the result of different practices, such as outdoor or indoor storage, climate differences, different biomass growth conditions.