This case series study aimed to investigate patients with insertional Achilles tendinopathy (IAT) who underwent radiofrequency (RF), how much do their patient-reported outcomes scores improve and what percentage return to sport, and what patient-related factors are associated with improved scores and increased odds of return to sport, at a minimum of 2-year follow-up. Between 2012 and 2018, 41 patients were followed up. The median Victorian Institute of Sports Assessment-Achilles (VISA-A) score increased from 20 (range, 3-62) to 97 (range, 53-100), the median 11-point visual analogue scale (VAS) reduced from 8 (range, 1-10) to 0 (range, 0-3) and the median Tenger score increased from 1 (range, 0-1) to 3 (range, 2-8). Thirty-eight (92.7%) patients returned to sports with a mean time of 11 ± 4.8 months. In linear regression analysis, age was significantly associated with return-to-sports outcome (b = -0.07, 95% CI = -0.13 to -0.02, p = 0.02), while in logistic regression, symptoms duration revealed a significant impact on pain presence (OR = 1.07, 95% CI = 1.01 to 1.14, p = 0.02). In summary, RF for IAT had a 68.7 ± 14.5 VISA-A improvement at 5.4 years of follow-up regarding reliable functional restoration and pain reduction; however, the current evidence remains insufficient to support RF as an effective treatment for IAT.