The C-glucosidic ellagitannins are found in wine as a result of its aging in oak barrels or in stainless steel tanks with oak chips. Once dissolved in this slightly acidic solution, the C-glucosidic ellagitannins vescalagin can react with nucleophilic entities present in red wine, such as ethanol, catechin, and epicatechin, to generate condensed hybrid products such as the β-1-O-ethylvescalagin and the flavano-ellagitannins (acutissimin A/B and epiacutissimin A/B), respectively. During this study, we first monitored the extraction kinetic and the evolution of the eight major oak-derived C-glucosidic ellagitannins in red wines aged in oak barrels or in stainless steel tank with oak chips. Their extraction rates appeared to be faster during red wine aging in stainless steel tanks with oak chips. However, their overall concentrations in wines were found higher in the wine aged in barrels. The formation rates of the vescalagin-coupled derivatives were also estimated for the first time under both red wine aging conditions (i.e., oak barrels or stainless steel tanks with oak chips). As observed for the oak-native C-glucosidic ellagitannins, the concentrations of these vescalagin derivatives were higher in the red wine aged in oak barrels than in stainless steel tanks with oak chips. Despite these differences, their relative composition was similar under both red wine aging conditions. Finally, the impact of the oak chips size and toasting level on the C-glucosidic ellagitannins concentration in wine was also investigated.