Background: Anastomotic coupling device (ACD) has reached wide popularity, especially in venous anastomosis of free-tissue transfers. There are scant reviews in the literature about the reliability of these devices in venous anastomosis. We retrospectively analyzed our free flap cases to compare the thrombosis rates between ACDs and handsewn anastomosis and other possible risk factors that may contribute to venous thrombosis. Materials and Methods: Data of all microvascular free-tissue transfers performed between January 2015 and August 2019 were retrospectively reviewed. Patient characteristics were recorded. Reconstruction characteristics such as venous anastomosis type (hand-sewn vs. anastomotic coupler device), reconstruction site, and number of surgical interventions were also recorded. Results: A total of 385 consecutive-free microvascular reconstructions were identified. Total venous thrombosis rate was 4.7%. There was no statistically significant difference between hand-sewn anastomosis and anastomosis with coupler device (5.2% vs. 3.2%, P = 0.58). Only reconstruction site was found to be significantly associated with higher venous thrombosis (P = 0.03). Discussion: Our results involving different reconstruction sites and including multiple flap types demonstrated comparable revision rates between ACDs and hand-sewn anastomosis. This finding is consistent with the current literature.