To investigate the flavour evolution mechanism of raw Pu-erh tea (RPT) during storage, the volatile and non-volatile compounds of RPT with different storage years (1–10 years) from the same raw material origin, manufacturer, and storage location in Wenshan Prefecture, Yunnan Province, were systematically analysed by HPLC, HS-SPME-GC-MS, and OAV. The results showed that both cluster analyses based on non-volatile and volatile compounds could classify RPT of different storage years into three ageing cycles, with key turning points in the third and eighth years of storage, which is also accompanied by the colour changing from green to orange or brown, the aroma changing from a faint scent to woody and ageing, the astringency diminishing, and the sweet and mellow increasing. Theophylline was identified as the potential marker of RPT stored 1–3 years, while (−)-catechin gallate, (−)-gallocatechin gallate, quercetin, and rutin as those for a storage of 9–10 years. The volatile compounds indicate a general trend of an initial increase followed by a decrease. Forty-four key aroma compounds (OAV ≥ 1) were identified. Eucalyptol, β-Caryophyllene, 2-Amylfuran, Copaene, Estragole, and α-Terpinene originated as potential markers for RPT stored 1–3 years, while (Z)-Linalool oxide (furanoid), α-Terpineol, Terpinen-4-ol, and cis-Anethol were for RPT stored 8–10 years. This study revealed the flavour characteristics and quality changes of RPT over the course of storage, and constructed a sensory flavour wheel, providing theoretical underpinnings for the quality control and assessment of RPT.