Background: Evidence suggests that sports team participation differentially relates to health-risk behaviors. Few studies have explored relationships among high-risk youth. Purpose: To examine associations between weekly sports team participation and health-risk behaviors (substance use, sexual risk-taking, violence involvement) among alternative high school (AHS) students. Methods: Data for this repeated cross-sectional analysis came from the 2001, 2004, 2007, and 2010 Minnesota Student Surveys (n = 2847 to 4596). Logistic regression was used to examine relationships between sports team participation and 14 outcomes. Interaction terms tested whether associations varied by survey year, gender, and/or race/ethnicity. Results: For males, sports team participation protected against most substance use outcomes and was associated with higher condom use. Female sports participants were less likely than nonparticipants to have ever had sex. For both genders, sports team participation was positively associated with gun carrying. No differences by race/ethnicity or year were found. Discussion: Further research is needed with AHS students who play sports to understand mixed findings from the current study and how to promote healthy behaviors through sports. Translation to Health Education Practice: Health education professionals are in ideal positions to work with school administrators and researchers to facilitate scientific inquiry and translate it into practice.