The feasibility of using a basis set approach to the study of quantum dissipative dynamics is investigated for the spin-boson model, a system of two discrete states linearly coupled to a harmonic bath. The infinite Hamiltonian is discretized to a finite number of degrees of freedom. Traditional basis set approach, in a multiconfiguration time-dependent Hartree context, is used to solve the time-dependent Schrodinger equations by explicitly including all the degrees of freedom ("system"+"bath"). Quantities such as the reduced density matrix are then evaluated via a quadrature summation/Monte Carlo procedure over a certain number of time-dependent wave functions. Numerically exact results are obtained by systematically increasing the number of bath modes used to represent the condensed phase environment, as well as other variational parameters (number of basis functions, configurations, etc.). The potential of the current method is briefly discussed.