The disappearance of the C-glycosidic ellagitannins over time can occur even in absence of oxygen and their disappearance rate seems to be affected by the presence of other ellagitannins in the media. The objective of this work was to study the influence of the presence of other ellagitannins and/or oxygen on the individual evolution of the main oak ellagitannins in simple model systems in order to understand their behaviours in more complex media, such as wine. In all the studied conditions, vescalagin disappeared faster than castalagin, highlighting its greater reactivity. Oxygen increased the individual disappearance rate, as also occurred when more than one type of ellagitannin was present, above all if the additional ellagitannin(s) contained the same conformation in C1 as vescalagin. Experimental data were fitted to a kinetic model considering both the oxygen-dependent and oxygen-independent reactions, making possible the comparison between individual compounds in different scenarios.