OBJECTIVE : This study sought to evaluate the self-reported and program director-reported comfort of graduating Canadian obstetrics and gynaecology residents in independently performing various surgical skills. METHODS : A Web-based survey was distributed to four cohorts of graduating obstetrics and gynaecology residents across Canada (2014-2017). Residents were asked to indicate their comfort level with independently performing 34 core surgical procedures by using a five-point Likert-type scale. A similar survey was sent to program directors. Comfort scores for residents and program directors were compared using quantitative and qualitative methods as appropriate (Canadian Task Force Classification II-3). RESULTS : Resident and program director survey response rates were 168 of 320 (52.5%) and 20 of 48 (41.7%), respectively. Residents were "comfortable" or "very comfortable" performing 7 of 13 (54%) gynaecology and 4 of 6 (67%) obstetrics List A procedures independently. Program directors reported that residents were "comfortable" or "very comfortable" performing 10 of 13 (77%) gynaecology and 4 of 6 (67%) obstetrics List A procedures. Compared with program directors, residents reported lower comfort with certain minimally invasive and obstetrics List A procedures (P < 0.05). Differences in comfort when performing several List A procedures were related to training program size and plans to pursue fellowship. Qualitative analysis revealed several major and minor themes supporting the dichotomy between residents' lack of comfort and program directors' expectation of comfort. CONCLUSIONS : Graduating residents were not comfortable performing many core surgical procedures independently. Additionally, program directors believed that trainees were more comfortable than they reported, and comfort varied according to program size and future fellowship plans. The new competency-based curriculum is an opportunity to address this gap.