Red wine quality is determined greatly by phenolic substances whose presence relies on extraction of grape skins and seeds during fermentation. Monitoring phenolic behaviour is beneficial for fermentation management because of the importance of maceration during red winemaking and its influence on phenolics that contribute to predominant red wine characteristics, such as colour, flavour and mouthfeel. Properly quantifying the kinetics associated, however, with red grape and wine phenolics is an intricate process. This review focuses on the extraction and ensuing reactions of principal phenolic substances during various stages of red winemaking as described by dynamic and spatial mathematical models. The extraction and reaction phenomena are concurrently influenced by several environmental and technological factors during fermentation, such as temperature, oxidation and mixing regimes, resulting in complex phenolic behaviour over time. As such, employing mathematical modelling is extremely useful for ascertaining the kinetic and spatial basis for phenolic behaviour, and the models significantly enhance the existing understanding of the extraction and reaction mechanisms of phenolic substances that are critical to red wine quality. Ultimately, this knowledge will allow for the development of predictive tools for phenolic extraction based on fruit composition and can potentially contribute to increased wine quality with optimised and sustainable production practices.