ImportanceThe surgeon-anesthesiologist teamwork and relationship is crucial to good patient outcomes. Familiarity among work team members is associated with enhanced success in multiple fields but rarely studied in the operating room.ObjectiveTo examine the association between surgeon-anesthesiologist dyad familiarity—as the number of times working together—with short-term postoperative outcomes for complex gastrointestinal cancer surgery.Design, Setting, and ParticipantsThis population-based retrospective cohort study based in Ontario, Canada, included adults undergoing esophagectomy, pancreatectomy, and hepatectomy for cancer from 2007 through 2018. The data were analyzed January 1, 2007, through December 21, 2018.ExposuresDyad familiarity captured as the annual volume of procedures of interest done by the surgeon-anesthesiologist dyad in the 4 years before the index surgery.Main Outcomes and MeasuresNinety-day major morbidity (any Clavien-Dindo grade 3 to 5). The association between exposure and outcome was examined using multivariable logistic regression.ResultsSeven thousand eight hundred ninety-three patients with a median age of 65 years (66.3% men) were included. They were cared for by 737 anesthesiologists and 163 surgeons who were also included. The median surgeon-anesthesiologist dyad volume was 1 (range, 0-12.2) procedures per year. Ninety-day major morbidity occurred in 43.0% of patients. There was a linear association between dyad volume and 90-day major morbidity. After adjustment, the annual dyad volume was independently associated with lower odds of 90-day major morbidity, with an odds ratio of 0.95 (95% CI, 0.92-0.98; P = .01) for each incremental procedure per year, per dyad. The results did not change when examining 30-day major morbidity.Conclusions and RelevanceAmong adults undergoing complex gastrointestinal cancer surgery, increasing familiarity of the surgeon-anesthesiologist dyad was associated with improved short-term patient outcomes. For each additional time that a unique surgeon-anesthesiologist dyad worked together, the odds of 90-day major morbidity decreased by 5%. These findings support organizing perioperative care to increase the familiarity of surgeon-anesthesiologist dyads.