Background: Several operative techniques exist for Achilles tendinopathy. The purpose of our study was to compare the clinical and functional outcomes of flexor hallucis longus (FHL) transfer and V-Y advancement for the treatment of chronic insertional Achilles tendinopathy. Methods: Retrospective chart review from 2010 to 2016 of patients that underwent FHL transfer or V-Y advancement for chronic insertional Achilles tendinopathy. Outcome measures were compared for these two procedures. Results: In total, 46 patients (49 ankles) with a mean age of 55.0 (range 33–73) years. Mean follow-up time 44.7 +/− 25.5 months. FHL group had 21 patients (21 ankles) with 89% satisfaction, 14% complication rate, final VAS of 0.4, final VISA-A of 89.1, subjective strength improvement following surgery of 78%, and 94% would recommend the procedure. V-Y group had 25 patients (28 ankles) with 74% subjective satisfaction, 21% complication rate, final VAS of 1.4, final VISA-A of 78.4, subjective strength improvement following surgery of 67%, and 84% would recommend the procedure. There was no significant difference in any of the results rates between the two groups (p >.05). Conclusion: V-Y advancement is comparable to FHL transfer for the operative management of insertional Achilles tendinopathy. Though our results trend towards less satisfactory results following V-Y advancement, we found high satisfaction rates with similar functional outcomes and complication rates in both operative groups. We suggest considering V-Y advancement as a viable option for the primary treatment of chronic insertional Achilles tendinopathy in patients who may not be an ideal candidate for FHL transfer.