The direct functionalization of C(sp3)-H bonds assisted by native carbonyl functional groups is a promising strategy for the streamlined synthesis of complex molecules. Here, we report native amide-directed C(sp3)-H alkynylation reactions using an electron-deficient iridium catalyst and an electron-deficient pyridone ligand. Under the optimized conditions, the C(sp3)-H alkynylation of terminal methyl groups and internal methylene groups of cyclobutane carboxamides afforded the desired products in moderate to good yields.