Numerous research studies have evaluated factors influencing the nature and levels of phenolics and polysaccharides in food matrices. However, in grape and wines most of these works have approach these classes of compounds individually. In recent years, the number of publications interconnecting classes have increased dramatically. The present review relates the last decade’s findings on the relationship between phenolics and polysaccharides from grapes, throughout the entire winemaking process up to evaluating the impact of their relationship on the red wine sensory perception. The combination and interconnection of the most recent research studies, from single interactions in model wines to the investigation of the formation of complex macromolecules, brings the perfect story line to relate the relationship between phenolics and polysaccharides from the vineyard to the glass. Grape pectin is highly reactive toward grape and grape derived phenolics. Differences between grape cultivars or changes during grape ripeness will affect the extractability of these compounds into the wines. Therefore, the nature of the grape components will be crucial to understand the subsequent reactions occurring between phenolics and polysaccharide of the corresponding wines. It has been demonstrated that they can form very complex macromolecules which affect wine color, stability and sensory properties.