Background: It remains unknown if flywheel-assisted squats can be reliably utilized to increase power outputs and if such outputs are related. Objectives: To compare assisted and unassisted flywheel squat peak power outputs, determine their reliability, and analyze the relationship of the delta difference between peak power outputs during the squats. Methods: Twenty male athletes attended the laboratory 6 times—performing 3 sets of 8 repetitions of assisted and unassisted squats during 2 familiarization sessions and then 3 sets of 8 repetitions during experimental sessions 3 to 6 (2 sessions for unassisted and assisted squat in randomized order, respectively). Results: Concentric and eccentric peak power were significantly greater during assisted squats (both P < .001, d = 1.59, d = 1.57, respectively). Rating of perceived exertion (P = .23) and eccentric:concentric ratio (P = .094) did not differ between squat conditions. Peak power measures obtained excellent reliability, while rating of perceived exertion and eccentric:concentric ratio estimates were rated as acceptable to good, with greater uncertainty. A large to very large correlation (r = .77) was found between concentric and eccentric peak power delta difference of assisted and unassisted squats. Conclusions: Greater concentric outputs during assisted squats induce greater eccentric outputs and obtain greater mechanical load. Peak power is a reliable metric for monitoring flywheel training, whereas the eccentric:concentric ratio should be used with caution. Eccentric and concentric peak power are strongly related during flywheel squats, evidencing the need to maximize the concentric output to enhance the eccentric output.