We studied the relationship between song repertoire size, territorial behavior, and nesting success in Pied Bush Chat (Saxicola caprata) in Haridwar (Himalayan foothills), India for three consecutive years (2013–2015). Our findings indicate song repertoire size is correlated with nesting success, but pre-nesting territory size, average territory size, and territorial conflicts are independent of song repertoire size. It may be inferred that larger territories are not necessarily better territories. The findings suggest that larger territory size is more susceptible to increased territorial conflict. Significant differences were apparent between territory size and territorial conflicts in the different stages of the nesting cycle. The findings suggest that larger territory size is more susceptible to increased territorial conflict. We propose that even if territorial conflicts are independent of song repertoire size, the amount of territorial conflict may be constrained by the stage of nesting cycle or size of the territory. Depending upon breeding requirements, male Pied Bush Chats tailor their territory sizes and territorial conflicts during the course of the breeding season.