Free microvascular tissue transfer has become a reliable and wellestablished technique in reconstructive surgery. Success rates greater than 95% are constantly reported in the literature. End-to-end anastomosis to the external jugular vein (EJ) is supposed to be equally successful as anastomosis to the internal jugular vein (IJ) in patients treated with selective neck dissection. No data has been published so far when the IJ had to be resected during neck dissection. The purpose of this study was to evaluate the success rate and complications of end-to-end anastomosis to the EJ in cases of (modified) radical neck dissection with resected IJ. A retrospective mono-center cohort study was performed. All patients with end-to-end anastomosis to either the IJ or EJ-system were reviewed. 423 free-tissue transfers performed between 2009 and 2016 were included. The overall success rate was 97.0% with an anastomotic revision rate due to venous thrombosis of 12.3%. In patients when the IJ had to be resected and the venous anastomosis was performed at the ipsilateral side to the EJ (n = 53), overall flap loss was significantly higher (5/53; 9.4%). The revision rate in these cases was 22.6%. Success rate of anastomosis to the EJ when the ipsilateral IJ was still intact was 100% (n = 20). Success rate when the anastomosis was performed at the contralateral side was 100%. End-to-end anastomosis to the EJ in cases with resected IJ is more likely to result in free flap loss. Furthermore, it is associated with a higher revision rate. Therefore, in cases with resected IJ, we suggest to plan the operation beforehand with anastomosis at the contralateral side whenever possible.