Chirality-induced spin selectivity (CISS) has the potential to control the spin dynamics of chiral molecules for applications in quantum information science. Here we investigate the effect of CISS on the spin dynamics of radical pair formation following photodriven hole transfer in a pair of donor-chiral bridge-acceptor (D-Bχ-A) enantiomers, where D = 2,2,6,6-tetramethyl[1,3]-dioxolo[4,5-f][1,3]benzodioxole, Bχ = (R)- or (S)-2,2'-dimethoxy-4,4'-diphenyl-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthalene, and A = naphthalene-(1,4:5,8)-bis(dicarboximide). The results are compared to those obtained on the corresponding achiral D-B-A reference molecule in which B = 2″,3',5',6″-tetramethyl-1,1':4',1″:4″,1‴-quaterphenyl. Photoexcitation of A in a randomly oriented sample of D-Bχ-A in glassy butyronitrile at 85 K results in subnanosecond two-step hole transfer from 1*A to D to form D•+-Bχ-A•-, which was characterized using time-resolved electron paramagnetic resonance (TREPR) spectroscopy at X (9.6 GHz), Q (34 GHz), and W (94 GHz) bands. The spectra show line shape changes that are characteristic of a ∼38% contribution of CISS to the spin dynamics of D•+-Bχ-A•- formation. The line shape changes resulting from CISS are particularly apparent in the TREPR spectra at X-band as predicted by recent theory. These results show that (1) CISS has a significant influence on radical pair dynamics initiated by photodriven hole transfer, which is complementary to our recent electron transfer results, and (2) CISS can be detected using TREPR on radical pairs that are randomly oriented relative to an external magnetic field.