There is increasing attention on the intersection of sports and politics, with a particular focus on tying owners’ political donations to organization-level outcomes. However, the extant research leverages within-league panels of donations over time, so we know little about inter-league heterogeneities of political donations. Furthermore, extant work does not explicitly investigate the effect of election cycles on owners’ donation patterns. These limitations create questions about the generalizability and model robustness of current research. This paper analyzes N = 2,789 donations made by 158 team owners across six professional sport leagues during the 2016, 2018, and 2020 election cycles. Models suggest that donations from WNBA owners were significantly smaller and went to more progressive recipients on average than donations from owners in other leagues. Results also suggest that donations from WNBA, NASCAR, and NHL owners became significantly more moderate during presidential election cycles than during the midterm election cycle. Implications for future research are discussed.