Introduction: To assess outcomes of FHL transfer and V-Y plasty for chronic Achilles rupture due to insertional Achilles tendinopathy. Materials and methods: A case series of 12 patients was conducted between 1st January 2017 and 31st December 2018. The patients had short flexor hallucis longus tendon transfer with gastrocnemius lengthening by V-Y plasty for Achilles tendon rupture. Patients were allowed full weight bearing at six weeks post-operatively, and were followed up at three months and six months post-operatively, when the range of motion of the ankle was examined, and the outcome was assessed using the EFAS score. Results: Of the 12 patients in the study, the majority were males; the mean age was 50.6±8.96 years. A significant improvement in dorsiflexion and plantarflexion was noted at the six-month follow-up compared to the three-month follow-up (P=<0.001 for both). When compared to the normal side, dorsiflexion and plantarflexion of the affected ankle were significantly less at three months but were comparable at six months post-operatively. A significant improvement was noted in the mean EFAS score at the sixmonth follow-up (25.5±5.71) compared to three months (18.6±0.90) post-surgery (P=0.001). Males were also noted to have significantly higher EFAS scores at their six-month follow-up than females (P=0.022). In contrast, a negative correlation was noted between the European Foot and Ankle Society (EFAS) score at the final follow-up and age (P=0.011). Conclusion: FHL tendon transfer with V-Y plasty in chronic Achilles rupture due to insertional Achilles tendinopathy is an effective procedure resulting in the restoration of the ankle range of motion and improvement in functional scores.