Understanding of photoinduced interfacial carrier dynamics in organic-transition metal dichalcogenides heterostructures is very important for the enhancement of their potential photoelectronic conversion efficiencies. In this work we have used density functional theory (DFT) calculations and DFT-based fewest-switches surface-hopping dynamics simulations to explore the photoinduced hole transfer and subsequent nonadiabatic electron-hole recombination dynamics taking place at the interface of pentacene and MoS2 in pentacene@MoS2. Upon photoexcitation the electronic transition mainly occurs on the MoS2 monolayer, which corresponds to moving an electron to the MoS2 conduction band. As a result, a hole is left in the valence band. This hole state is energetically lower than certain occupied states of the pentacene molecule; thus, the interfacial hole transfer from MoS2 to pentacene is favorable in energy. In terms of nonadiabatic dynamics simulations, the hole transfer time to the HOMO-1 state of the pentacene is estimated to be about 600 fs; however, the following hole relaxation process from HOMO-1 to HOMO takes much longer time of ca. 15 ps due to the large energy gap between HOMO-1 and HOMO. Moreover, our results also show that the subsequent radiationless recombination process between the hole transferred to the pentacene molecule and the remaining electron on the MoS2 CBM needs about 10.2 ns. The computational results shed important mechanistic insights on the interfacial carrier dynamics of mixed-dimensional pentacene@MoS2. These insights could help to design excellent interfaces for organic-TMDs heterostructures.