Physician misconduct adversely affects patient safety and is therefore of societal importance. Little work has specifically examined re-disciplined physicians. A study was conducted to compare the characteristics of re-disciplined to first-time disciplined physicians. A retrospective review of Canadian physicians disciplined by medical boards between 2000 and 2015 was conducted. Physicians were divided into those disciplined once and those disciplined more than once. Differences in demographics, transgressions, and penalties were evaluated. There were 938 disciplinary events for 810 disciplined physicians with 1 in 8 (n = 101, 12.5%) being re-disciplined. Re-disciplined physicians had up to six disciplinary events in the study period and 4 (4.0%) had events in more than one jurisdiction. Among those re-disciplined, 94 (93.1%) were male, 34 (33.7%) were international medical graduates, and 88 (87.1%) practiced family medicine (n = 59, 58.4%), psychiatry (n = 11, 10.9%), surgery (n = 9, 8.9%), or obstetrics/gynecology (n = 9, 8.9%). The proportion of obstetrician/gynecologists was higher among re-disciplined physicians (8.9% vs. 4.2%, p = 0.048). Re-disciplined physicians had more mental illness (1.7% vs. 0.1%, p = 0.01), unlicensed activity (19.2% vs. 7.2%, p <0.01), and less sexual misconduct (20.1% vs. 27.9%, p = 0.02). License suspension occurred more frequently among those re-disciplined (56.8% vs. 48.0%, p = 0.02) as did license restriction (38.4% vs. 26.7%, p <0.01). License revocation was not different between cohorts (10.9% vs. 13.5%, p = 0.36). Re-discipline is not uncommon and underscores the need for better identification of at-risk individuals and optimization of remediation and penalties. The distribution of transgression argues for a national disciplinary database that could improve communication between jurisdictional medical boards.