Donor-acceptor dyads are promising materials for improving triplet-sensitized photon upconversion due to faster intramolecular energy transfer (ET), which unfortunately competes with charge transfer (CT) dynamics. To circumvent the issue associated with CT, we propose a novel purely organic donor-acceptor dyad, where the CT character is confined within the donor moiety. In this work, we report the synthesis and characterization of a stable organic radical donor-triplet acceptor dyad () consisting of the acceptor perylene () linked to the donor (4--carbazolyl-2,6-dichlorophenyl)-bis(2,4,6-trichlorophenyl)methyl radical (). Upon red-excitation of , the doublet emission of the donor () is significantly quenched, and a recorded delayed emission centered at ca. 490 nm was attributed to the fluorescence emission from the acceptor. Time-resolved transient absorption spectroscopy suggests doublet-to-triplet energy transfer (DTET) dynamics from the donor to the acceptor as the time constant τ for the donor transient species decreases from 21.47 ns for the sensitizer to 8.73 ns for dyad. This process is accompanied by the appearance of a long-lived component with τ = 97.06 ns, which we ascribe to the triplet transient of the acceptor . Furthermore, computational results indicate that the DTET is intramolecular as computed spin densities of the quartet state show unpaired electrons of ρ ≈ 1 on the donor and of ρ ≈ 2 on the acceptor . The present study highlights the possibility to employ doublet chromophoric systems for light-harvesting and energy upconversion, which can be further tailored for several optoelectronic applications.