The risk of antisocial outcomes in individuals with personality disorder (PD) remains uncertain. The authors synthesize the current evidence on the risks of antisocial behavior, violence, and repeat offending in PD, and they explore sources of heterogeneity in risk estimates through a systematic review and meta-regression analysis of observational studies comparing antisocial outcomes in personality disordered individuals with controls groups. Fourteen studies examined risk of antisocial and violent behavior in 10,007 individuals with PD, compared with over 12 million general population controls. There was a substantially increased risk of violent outcomes in studies with all PDs (random-effects pooled odds ratio [OR] = 3.0, 95% CI = 2.6 to 3.5). Meta-regression revealed that antisocial PD and gender were associated with higher risks (p = .01 and .07, respectively). The odds of all antisocial outcomes were also elevated. Twenty-five studies reported the risk of repeat offending in PD compared with other offenders. The risk of a repeat offense was also increased (fixed-effects pooled OR = 2.4, 95% CI = 2.2 to 2.7) in offenders with PD. The authors conclude that although PD is associated with antisocial outcomes and repeat offending, the risk appears to differ by PD category, gender, and whether individuals are offenders or not.