We investigate bipartite entanglement in random quantum XY models at equilibrium. Depending on the intrinsic time scales associated with equilibration of the random parameters and measurements associated with observation of the system, we consider two distinct kinds of disorder, namely annealed and quenched. We conduct a comparative study of the effects of disorder on nearest-neighbor entanglement, when the nature of randomness changes from being annealed to quenched. We find that entanglement properties of the annealed and quenched systems are drastically different from each other. This is realized by identifying the regions of parameter space in which the nearest-neighbor state is entangled, and the regions where a disorder-induced enhancement of entanglement —order-from-disorder— is obtained. We also analyze the response of the quantum phase transition point of the ordered system with the infusion of disorder.