The promise of wearable and implantable devices has made stretchable organic semiconductors highly desirable. Though there are increasing attempts to design intrinsically stretchable conjugated polymers, their performance in terms of charge carrier mobility and maximum fracture strain is still lacking behind extrinsic approaches (i.e., buckling, Kirigami interconnects). Here, polymer crosslinking with flexible oligomers is applied as a strategy to reduce the tensile modulus and improve fracture strain, as well as fatigue resistance for a high mobility diketopyrrolopyrrole polymer. These polymers are crosslinked with siloxane oligomers to give stretchable films stable up to a strain epsilon = 150% and 500 strain-and-release cycles of 100% strain without the formation of nanocracks. Organic field-effect transistors are prepared to assess the electrical properties of the crosslinked film under cyclic strain loading. An initial average mobility (mu(avg)) of 0.66 cm(2) V-1 s(-1) is measured at 0% strain. A steady mu(avg) above 0.40 cm(2) V-1 s(-1) is obtained in the direction perpendicular to the strain direction after 500 strain-and-release cycles of 20% strain. The mu(avg) in the direction parallel to strain, however, is compromised due to the formation of wrinkles.