Vascular anastomoses typically involve a handsewn technique requiring significant surgical training, expertise, and time. The aim of our systematic review was to identify and describe sutureless vascular anastomosis techniques. We performed a systematic review of all sutureless vascular anastomosis technologies published in MEDLINE, PubMed, Embase, CINAHL, Cochrane, Web of Science, and Scopus Library databases and a patent review using US Patent and Trade Office Application, US Patent and Trademark Office Patent, Google Patents, Lens, Patent Quality Through Artificial Intelligence, SureChEMBL, and E-Space Net. Data from inclusion studies and patents published between January 1, 1980 and July 15, 2021 were abstracted to describe their category, anastomosis type and configuration, study types, and advantages and disadvantages encountered with each technology. Two hundred eleven original studies and 475 patents describing sutureless vascular anastomosis technologies were identified. In the literature, stents/stent–grafts/grafts (n = 61), lasers (n = 53), and couplers (n = 27) were the predominant device categories. In the patent review, adhesive technologies (n = 103), stents/stent–grafts/grafts (n = 68), and mechanical connectors (n = 61) predominated. The majority of studies involved in vivo animal studies (n = 193); 32.2% (n = 68) of investigations involved human trials; and 17.9% (n = 85) of patent technologies were approved by the US Food and Drug Administration. The main advantages described for sutureless anastomosis technologies included faster procedure time and greater patency rates compared with handsewn anastomoses. The main disadvantages included reduced vessel compliance, stenosis, leakage, and device costs. The appeal of sutureless technology is substantiated by numerous animal trials, but their use in humans remains limited. This may be a reflection of strict regulatory criteria and/or vascular complications associated with currently available technologies.