In this paper, we study the effect of classical driving field on the spontaneous emission spectrum of a qubit embedded in a dissipative cavity. Furthermore, we monitor the entanglement dynamics of the driven qubit with its radiative decay under the action of the classical field. Afterwards, we carry out an investigation on the possibility of entanglement swapping between two such distinct driven qubits. The swapping will be feasible with the aid of a Bell state measurement performing on the photons leaving the cavities. It is demonstrated that the classical driving field has a beneficial effect on the prolonging of the swapped entanglement.