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Abstract Background Extensive literature exists about the treatment of ankle osteochondral lesions, but there is no specific review of retrograde drilling, despite its common application. Indications for retrograde drilling are still few and are far from clear, and some evolutions of the technique have recently occurred. The aim of this review is to provide an update on actual applications and techniques of retrograde drilling for ankle osteochondral lesions. Methods A systematic review was carried out according to the 2020 PRISMA guidelines. The PubMed and Embase databases were searched in June 2023. The search string focused on studies related to retrograde drilling in the treatment of ankle osteochondral lesions. Results Twenty-one articles for a total of 271 ankles were included in this review. The mean length of the treated lesions was 11.4 mm. Different navigation systems were used, with fluoroscopy the most commonly used. Various adjuvants were employed after drilling, with bone graft the most commonly applied. In most cases, postoperative patient satisfaction and symptom relief were reported, and no complications occurred. Retrograde drilling was found to be suitable for the treatment of subchondral cysts with intact cartilage or small lesions. Some modifications to the original technique may allow surgical indications to be extended to more complex cases. Conclusions Middle-term results of retrograde drilling showed postoperative satisfaction and symptom relief with both original and modified techniques. Additional research is required to investigate the long-term results. Level of evidence: IV. Trial registration: This systematic review was registered on PROSPERO (id number: CRD42022371128).