The regiodivergent catalytic dehydrogenative cross-coupling reactions at both sp² and sp³ hybridized carbons of aromatic compounds are particularly challenging. Herein, we report the finding of transient directing group controlled regiodivergent C(sp³)–C(sp²) and C(sp²)–C(sp²) cross-coupling in the o-methyl benzaldehyde frameworks. Catalyzed by palladium, using K₂S₂O₈ or [F⁺] reagents as by-standing oxidants and unactivated arenes as substrates/solvents, various benzyl benzaldehydes or phenyl benzaldehydes were prepared. A mechanism study indicated that the regiospecificity is dominated by the [5,6]-fused palladacycle or [6,5]-fused palladacycle intermediates, which are generated from Pd-chelation with specified transient directing groups and further C–H activations.