The Ostrogorski paradox refers to the fact that, facing finitely many dichotomous issues, choosing issue-wise according to the majority rule may lead to a majority defeated overall outcome. This paper investigates the possibility for a similar paradox to occur under alternative specifications of the collective preference relation. The generalized Ostrogorski paradox occurs when the issue-wise majority rule leads to an outcome which is not maximal according to some binary relation φ defined over pairs of alternatives. We focus on three possible definitions of φ, whose sets of maximal elements are respectively the Uncovered Set, the Top-Cycle, and the Pareto Set. We prove that a generalized paradox may prevail for the Uncovered Set. Moreover, it may be avoided for the same issue-wise majority margins as for the Ostrogorski paradox. However, the issue-wise majority rule always selects a Pareto-optimal alternative in the Top-Cycle.