This study evaluated the relationship between cell wall breakdown, from Shiraz grapes harvested at three different ripeness levels and the colour and phenolics extracted during alcoholic fermentation into wines. Phenolic differences between the ripeness treatments were minimal after ¼ of the fermentation was completed. However, colour and phenolic content were significantly higher in finished wines made from 25°Brix grapes compared to those from 21°Brix and 23°Brix. Levels of grape cell wall polysaccharide deconstruction during fermentation was a determining correlative factor in relation to phenolic extractability. In this context, the de-pectination observed during ripening was found to enhance this deconstruction or “opening-up” of the grape pomace during fermentation, thus increasing the differential extraction of specific polyphenols, especially polymeric polyphenols, into the wines. Additionally, the degree of cell wall deconstruction seemed to play a role in the possible retention and extraction of specific grape proanthocyanidins, depending on their nature and polymer length.