In laparoscopic surgery, surgeons should develop several manual laparoscopic skills before carrying out real operative procedures using a low-cost box trainer. The Fundamentals of Laparoscopic Surgery (FLS) program was developed as a program to assess fundamental knowledge and surgical skills, required for basic laparoscopic surgery. The peg transfer task is a hands-on exam in the FLS program that assists a trainee to understand the relative minimum amount of grasping force necessary to move the pegs from one place to another place without dropping them. In this paper, an autonomous, sequential assessment algorithm based on deep learning, a multi-object detection method, and, several sequential If-Then conditional statements have been developed to monitor each step of a surgeon’s performance. Images from three different cameras are used to assess whether the surgeon executes the peg transfer task correctly and to display a notification on any errors on the monitor immediately. This algorithm improves the performance of a laparoscopic box-trainer system using top, side, and front cameras and removes the need for any human monitoring during a peg transfer task. The developed algorithm can detect each object and its status during a peg transfer task and notifies the resident about the correct or failed outcome. In addition, this system can correctly determine the peg transfer execution time, and the move, carry, and dropped states for each object by the top, side, and front-mounted cameras. Based on the experimental results, the proposed surgical skill assessment system can identify each object at a high score of fidelity, and the train-validation total loss for the single-shot detector (SSD) ResNet50 v1 was about 0.05. Also, the mean average precision (mAP) and Intersection over Union (IoU) of this detection system were 0.741, and 0.75, respectively. This project is a collaborative research effort between the Department of Electrical and Computer Engineering and the Department of Surgery, at Western Michigan University.