The longtime behavior of weakly interacting bosons moving in a two-dimensional optical lattice and coupled to a lossy cavity is investigated numerically via the truncated Wigner method, which allows us to take into full account the dynamics of the cavity mode, quantum fluctuations, cavity-boson correlations, and self-organization of individual runs. We first compare our results for small systems with quasi-exact calculations based on quantum trajectories, finding a remarkably good agreement for experimentally relevant boson fillings that improves further with system size. For large systems, we observe metastability at very long times and superfluid quasi–long range order, in sharp contrast with the true long range order found in the ground state of the approximate Bose-Hubbard model with extended interactions, obtained by adiabatically eliminating the cavity field. As the strength of the light-matter coupling increases, the system first becomes supersolid at the Dicke superradiant transition and then turns into a charge-density wave via the Berezinskii-Kosterlitz-Thouless mechanism. The two phase transitions are characterized via an accurate finite-size scaling analysis.