The impact of family military involvement on adolescent mental health and substance abuse is well established, but little is known about other behavioral health outcomes such as physical fighting. We assessed the relationship between family military involvement and physical fighting in a representative sample of 3,928 high school students. Weighted logistic regression was used to determine whether adolescents from military families had higher odds of fighting and fighting on school property compared with adolescents of non-military families after controlling for demographics, substance use, depressive symptoms, and bullying victimization. We also assessed the cumulative impact of multiple risk factors on fighting outcomes. Overall, 23.5% of high school students reported physical fighting and 7.0% reported physical fighting at school. Youth from military families had higher odds of physical fighting (adjusted odds ratios [AOR] = 1.69; 95% confidence interval [CI] = [1.27, 2.25]) and physical fighting on school property (AOR = 1.98; 95% CI = [1.16, 3.39]). In models stratified by gender, family military involvement remained independently associated with physical fighting and physical fighting at school for males (AOR = 1.74; 95% CI = [1.15, 2.65] and AOR = 2.21; 95% CI = [1.03, 4.74]) and females (AOR = 1.65; 95% CI = [1.11, 2.45] and AOR = 1.88; 95% CI = [1.01, 3.50]). The odds of engaging in each physical fighting outcome increased as the cumulative number of risk factors increased. School-based interventions aimed at addressing fighting should be tailored to fit the unique needs of adolescents in military families, particularly those with additional risk factors.