Colloidal semiconductor nanocrystals as triplet photosensitizers are characterized by a negligible intersystem crossing energy loss as compared to that of traditional molecular sensitizers. This property in principle allows for a large apparent anti-Stokes shift in sensitized triplet-triplet annihilation photon upconversion (TTA-UC) for a variety of applications. In previous systems, however, this advantage is largely erased by the energy loss associated with energy transfer from nanocrystals to surface-anchored triplet transmitter molecules. Here we report visible-to-ultraviolet TTA-UC from 473 to 355 nm, corresponding to an apparent anti-Stokes shift of 0.87 eV, with a quantum efficiency that reaches 4.5% (normalized at 100%). The system consists of CsPbBr3 nanocrystal sensitizers, phenanthrene transmitters, and diphenyloxazole annihilators. Time-resolved spectroscopy reveals that triplet energy transfer from CsPbBr3 nanocrystals to phenanthrene can be endothermic yet efficient thanks to a sizable entropic gain. This study exemplifies how entropic effects can be harnessed to enhance or control a plethora of applications with nanocrystals as photosensitizers.