We investigate the dynamical phases and phase transitions arising in a classical two-dimensional anisotropic XY model under the influence of a periodically driven temporal external magnetic field in the form of a symmetric square wave. We use a combination of finite temperature classical Monte Carlo simulation, implemented within a CPU+GPU paradigm, utilizing local dynamics provided by the Glauber algorithm and a phenomenological equation-of-motion approach based on relaxational dynamics governed by the time-dependent free energy within a mean-field approximation to study the model. We investigate several parameter regimes of the variables (magnetic field, anisotropy, and the external drive frequency) that influence the anisotropic XY system. We identify four possible dynamical phases: Ising-SBO, Ising-SRO, XY-SBO, and XY-SRO. Both techniques indicate that only three of them (Ising-SRO, Ising-SBO, and XY-SRO) are stable dynamical phases in the thermodynamic sense. Within the Monte Carlo framework, a finite-size scaling analysis, shows that XY-SBO does not survive in the thermodynamic limit giving way to either an Ising-SBO or a XY-SRO regime. The finite-size scaling analysis further shows that the transitions between the three remaining dynamical phases either belong to the two-dimensional Ising universality class or are first-order in nature. Within the mean-field calculations yield three stable dynamical phases, i.e., Ising-SRO, Ising-SBO and XY-SRO, where the final steady state is independent of the initial condition chosen to evolve the equations of motion, as well as a region of bistability where the system flows to either Ising-SBO or XY-SRO (Ising-SRO) depending on the initial condition. Unlike the stable dynamical phases, the XY-SBO represents a transient feature that is eventually lost to either Ising-SBO or XY-SRO. Our mean-field analysis highlights the importance of the competition between switching of the stationary point(s) of the free energy after each half cycle of the external field and the two-dimensional nature of the phase space for the equations of motion.