Artificial intelligence (AI) has the potential to improve healthcare and patient safety and is currently being adopted across various fields of medicine and healthcare. AI and in particular computer vision (CV) are well suited to the analysis of minimally invasive surgical simulation videos for training and performance improvement. CV techniques have rapidly improved in recent years from accurately recognizing objects, instruments, and gestures to phases of surgery and more recently to remembering past surgical steps. Lack of labeled data is a particular problem in surgery considering its complexity, as human annotation and manual assessment are both expensive in time and cost, and in most cases rely on direct intervention of clinical expertise. In this study, we introduce a newly collected simulated Laparoscopic Surgical Performance Dataset (LSPD) specifically designed to address these challenges. Unlike existing datasets that focus on instrument tracking or anatomical structure recognition, the LSPD is tailored for evaluating simulated laparoscopic surgical skill performance at various expertise levels. We provide detailed statistical analyses to identify and compare poorly performed and well-executed operations across different skill levels (novice, trainee, expert) for three specific skills: stack, bands, and tower. We employ a 3-dimensional convolutional neural network (3DCNN) with a weakly-supervised approach to classify the experience levels of surgeons. Our results show that the 3DCNN effectively distinguishes between novices, trainees, and experts, achieving an F1 score of 0.91 and an AUC of 0.92. This study highlights the value of the LSPD dataset and demonstrates the potential of leveraging 3DCNN-based and weakly-supervised approaches to automate the evaluation of surgical performance, reducing reliance on manual expert annotation and assessments. These advancements contribute to improving surgical training and performance analysis.