Paradoxical leadership and ambidextrous leadership have been documented as effective leadership approaches in handling managerial tensions and have largely proliferated in parallel in the past decade. Little has been known about how paradoxical leadership is distinguished from ambidextrous leadership. This paper integrates the contingency perspective with paradox theory to establish their distinctions in four studies. A meta-analytic study (Study 1) finds that paradoxical leadership has a stronger effect on employee creativity and a weaker effect on job strain than ambidextrous leadership. However, the findings cannot be replicated in an experience sampling method study (Study 2). The mixed findings between Studies 1 and 2 beget one possible explanation: the advantage of paradoxical leadership over ambidextrous leadership could be theoretically bounded to specific conditions. To test the theoretical boundary explanation, two experiments (Study 3) are conducted and reveal that paradoxical leaders handle structural tensions (versus contextual tensions) better (versus worse) than ambidextrous leaders, which is reflected in higher employee creativity and lower employee job strain.