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The understanding of the structure‐mechanical property relationship for semiconducting polymers is essential for the application of flexible organic electronics. Herein pseudo free‐standing tensile testing, a technique that measures the mechanical property of thin films floating on the surface of water, is used to obtain the stress–strain behaviors of two semiconducting polymers, poly(3‐hexylthiophene) (P3HT) and poly(2,5‐bis(2‐decyltetradecyl)‐3,6‐di(thiophen‐2‐yl)diketopyrrolo[3,4‐c]pyrrole‐1,4‐dione‐alt‐thienovinylthiophene (DPP‐TVT) donor–acceptor (D–A) polymer. To our surprise, DPP‐TVT shows similar viscoelastic behavior to P3HT, despite DPP‐TVT possessing a larger conjugated backbone and much higher charge carrier mobility. The viscoelastic behavior of these polymers is due to sub room temperature glass transition temperatures (T_g), as shown by AC chip calorimetry. These results provide a …