Introduction: Emergency medicine (EM) residents are expected become proficient in a number of rarely performed, high risk procedures. We developed Critical Care Skills Training Day for senior FRCP and CCFP EM residents at a single university program to fill a gap in resident confidence with these procedures. The day applies principles of deliberate practice with focused feedback using simulation-based training for several rarely performed procedures including thoracotomy, fibre-optic intubation, pericardiocentesis, resuscitative hysterotomy and central line insertion. The objectives of this work was to improve the residents’ scores of self-perceived comfort independently performing these procedures by completion of the training day. Methods: Clinician educators, residency program directors and simulation specialists designed and taught the curriculum. We used pre- and post-training day surveys blending Likert, multiple choice and free text comments to measure comfort performing each procedure, overall satisfaction and usefulness of this training. Descriptive statistics were used to analyze results. Pre-post differences were assessed using paired sample T-tests. Comments and themes from course evaluations were used to make yearly iterative changes. Results: A total of 95 residents completed the curriculum between 2016-2018. 89 completed evaluations (93%). Residents reported significant (p < 0.05) improvement in comfort independently performing fibre optic intubation, thoracotomy and central line insertion. The day was rated very highly, 9.4/10 (SD, 0.72), over 3 years. Feedback was positive with participants identifying opportunities for repeated practice, feedback from instructors and practical tips to improve performance as valuable aspects. Iterative changes were made yearly in response to resident feedback including introduction of new procedures, incorporating skills into sim-based cases, and different training models for skill training. Conclusion: Critical Care Skills Training Day for EM residents was created using the principle of deliberate practice to fill a perceived gap in resident training. Residents who completed the annual curriculum showed a marked increase in comfort independently performing several of the procedures. Ongoing challenges include the length of the day, economies of scale, and training models available for the rare procedures. Future directions include the integration of longitudinal objective performance evaluations to align with the competency by design curriculum.