Abstract Background End-to-side (ES) venous anastomosis is an established approach for head and neck reconstruction and has several benefits over conventional end-to-end (EE) anastomosis. However, this is not preferred by all, which may be due to technical preferences for an EE anastomosis by many surgeons. We present here our experience of routine ES venous anastomosis for head and neck reconstruction over the past 8 years. Materials and Methods All consecutive head and neck malignancy patients reconstructed with free flap and our routine ES internal jugular vein (IJV) anastomosis approach between 2015 and 2023 have been included in this study. Flap-related variables are reviewed retrospectively. Results Reconstruction was done with a total of 585 free flaps including 303 radial forearm flaps (RFFs), 143 osteocutaneous fibula flaps (OCFFs), and 139 anterolateral thigh (ALT) flaps. The flap survival rate was 573/585 (97.95%). Re-exploration and salvage rates were 45/585 (7.69%) and 38/45, respectively (84.44%). Conclusion Routine use of ES anastomosis simplifies microvascular anastomosis by avoiding efforts related to the selection of recipient vessels, providing a single large-caliber venous outlet, the favorable geometric orientation of the pedicle, and ease of re-exploration. The vascular anastomosis for RFF, ALT, and OCFF flap is feasible with 7–0 sutures and under 4.5X loupe magnification with this approach quite conveniently with similar outcomes to the reported flap survival rate in the contemporary practice.