The extraction of phenolic compounds during maceration is of utmost importance in red winemaking. However, the monitoring of phenolic extraction is often hampered by analytical and statistical constraints. The aim of this study was to monitor phenolic extraction kinetics with the use of PLS phenolic calibrations and batch statistical process control. Eight batches of Cabernet Sauvignon and Shiraz grapes during alcoholic fermentation under different maceration conditions (pressing at 1/3rd, 2/3rd and end of fermentation) and punch down regimes (low vs. high frequency) were evaluated in the study. Cabernet Sauvignon appeared to be a more suitable cultivar for longer maceration conditions with increased tannin extraction observed. Similar trends were observed for punch down for both cultivars. The use of PLS calibrations and batch level modelling provided an enhanced interpretation and understanding of phenolic extraction during red wine fermentations.