In condensed solids, triplet exciton migration and succeeding triplet–triplet annihilation (TTA) are major bottleneck processes for efficient photon upconversion (UC) using sunlight excitation. We theoretically investigated the reaction times of TTA and the triplet–triplet energy transfer (TTET) as the elementary processes of triplet exciton migration in organic crystals of two molecular species: 9,10-diphenylanthracene (DPA) and its double-strapped alkyl derivative (C7-sDPA) as the models of a recently reported crystalline system of TTA-UC by Kamada et al. The reaction times calculated based on Marcus theory clarified that the dimensionality of TTET and synergetic effects of TTA and TTET are responsible for the high UC quantum yield as well as their triplet lifetimes.