We numerically investigate the gravitational waves generated by the head-on collision of equal-mass, self-gravitating, real scalar field solitons (oscillatons) as a function of their compactness $\mathcal{C}$. We show that there exist three different possible outcomes for such collisions: (1) an excited stable oscillaton for low $\mathcal{C}$, (2) a merger and formation of a black-hole for intermediate $\mathcal{C}$, and (3) a pre-merger collapse of both oscillatons into individual black-holes for large $\mathcal{C}$. For (1), the excited, aspherical oscillaton continues to emit gravitational waves. For (2), the total energy in gravitational waves emitted increases with compactness, and possesses a maximum which is greater than that from the merger of a pair of equivalent mass black-holes. The initial amplitudes of the quasi-normal modes in the post-merger ring-down in this case are larger than that of corresponding mass black-holes – potentially a key observable to distinguish black-hole mergers with their scalar mimics. For (3), the gravitational wave output is indistinguishable from a similar mass, black-hole–black-hole merger.