The influence of grape maturity on wine volatome was investigated using HS-SPME-GC × GC-TOFMS. Shiraz wines were made from grapes harvested from four different vineyards from two berry maturity levels. A total of 1276 putative compounds were detected in at least one of the wine samples and 175 showed significant trends related to grape maturity. The first two dimensions of the Principal component analysis accounted for 57% of the variation and separated the samples according to the harvest date. Wines from the first harvest date were characterised by an abundance of lipoxygenase derived compounds, norisoprenoids and sulfur-containing compounds whereas a significant increase in some acetate esters was observed in wines produced from the more mature grapes. This study demonstrated a common evolution of grape volatiles for Shiraz inside the same mesoclimate. During the late ripening stage of the grape, a direct nexus between sugar concentration and wine volatile evolution was not observed.