Tannins have always been the subject of great interest for their countless properties, first of all their ability to produce functional coatings on a variety of materials. We report herein a comparative evaluation of the antioxidant properties of wood tannin-based coated substrates. In particular, nylon membrane filters were functionalized with chestnut (hydrolyzable) or quebracho (condensed) tannins by dip coating under different conditions. The efficiency of functionalization was evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing/antioxidant power (FRAP) assays, which invariably highlighted the superior ability of condensed tannins to induce the formation of a functional and robust coating. The results of the antioxidant assays revealed also the deleterious effects of aerial or enzymatic oxidation conditions on substrate functionalization, being more significant in the case of hydrolyzable tannins. On the other hand, the use of oxidizing conditions allowed to obtain more stable coatings, still exhibiting good antioxidant properties, in the case of condensed tannins. The presence of iron ions did not lead to a significant improvement of the coating efficiency for either tannins. The systematic approach used in this work provides novel and useful information for the optimal exploitation of tannins in antioxidant functional coatings.