Simulation has been recognized for its ability to develop competency-level skills and as a replacement for some introductory fieldwork (FW) hours. This study explored how occupational therapy competency-related skills developed over sequential in-person simulations across health practice contexts during Level 1 FW. Entry-to-practice occupational therapy students (N = 66) participated in six sequential, formative, Level 1 FW simulations. The first three sequential simulations (the same patient case evolves in each successive interaction) included a trained simulated patient in a community mental health context and the following three engaged a trained simulated inpatient in a physical health context. Evaluation rubric variables included selected Competencies for Occupational Therapists in Canada (2021) scaffolded to performance expectations at an introductory Level 1 FW placement level. Quantitative pre-post comparison design with secondary data analysis was analyzed using Wilcoxon signed-rank test and ordered logistic regression. Each additional simulation demonstrated significant increases in the odds of improved performance in clinical skills, clinical decision making, responding to evolving patient's needs and priorities, identifying their own strengths and weaknesses, articulating clinical reasoning, and receiving constructive criticism. However, students' skills in the physical health context for decision-making and responding to the patient's needs and priorities did not demonstrate the same improvement trajectories as the mental health context. Sequential simulations are an effective modality for developing Level 1 competency related skills in different practice contexts. Depending on the competency-related practice skill and context, three or more formative unfolding simulations in that context may be needed for a significant improvement.