(1) Background: In the last few years, technological developments in the surgical field have been rapid and are continuously evolving. One of the most revolutionizing breakthroughs was the introduction of the IoT concept within surgical practice. Our systematic review aims to summarize the most important studies evaluating the IoT concept within surgical practice, focusing on Telesurgery and surgical Telementoring. (2) Methods: We conducted a systematic review of the current literature, focusing on the Internet of Surgical Things in Telesurgery and Telementoring. Forty-eight (48) studies were included in this review. As secondary research questions, we also included brief overviews of the use of IoT in image-guided surgery, and patient Telemonitoring, by systematically analyzing fourteen (14) and nineteen (19) studies, respectively. (3) Results: Data from 219 patients and 757 healthcare professionals were quantitively analyzed. Study designs were primarily observational or based on model development. Palpable advantages from the IoT incorporation mainly include less surgical hours, accessibility to high quality treatment, and safer and more effective surgical education. Despite the described technological advances, and proposed benefits of the systems presented, there are still identifiable gaps in the literature that need to be further explored in a systematic manner. (4) Conclusions: The use of the IoT concept within the surgery domain is a widely incorporated but less investigated concept. Advantages have become palpable over the past decade, yet further research is warranted.