The traditional ageing of wine spirits is done in wooden barrels, however, high costs have led to the search for alternative technologies, such as the use of stainless steel tanks with wooden staves and the application of micro-oxygenation. This work evaluates the changes in the major volatile compounds of wine spirits aged for 6, 12 and 18 months in wooden barrels and stainless steel tanks with micro-oxygenation. For both ageing technologies, two types of wood (Limousin oak and Portuguese chestnut wood) were used. The samples were analysed concerning their alcohol strength (electronic densimetry) and volatile composition, namely of methanol, acetaldehyde, ethyl acetate and other major volatile compounds ((GC-FID) and near-infrared spectroscopy (NIR)). The results show that the ageing technology was more influential than the wood species for the volatile composition of wine spirits, namely acetaldedehyde, methanol, 2-methylpropan-1-ol and 2+3-methylbutan-1-ol. However, the opposite behaviour was found for the spectral data. The ageing process was accelerated by using the alternative ageing technology, especially with chestnut wood staves. The most informative spectral regions to discriminate samples were around 6859 cm−1 and from 5200 cm−1 to 4200 cm−1. NIR is a promising technique to identify different technologies and different wood species used in the ageing process of wine spirits.