This work explores the reactivity of singlet oxygen with respect to two typical reactions: cycloaddition to anthracene and excitation energy transfer (EET) to a carotenoid using diabatic states with multistate density functional theory (MSDFT). Noticeably, the degenerate state 1Δg has distinct open-shell (OS) and closed-shell (CS) components, and the closed-shell component showed more reactivity than the open-shell one due to the strong diabatic couplings to the product diabatic states. The diabatic perspective presented in this work could also apply to general singlet fission processes.