When femoral head chondropaties are located medially or parafoveal, they pose a challenge to arthroscopically reach the affected area through commonly used portals. Though surgical hip dislocation remains as the gold standard for treatment of such lesions, many patients reject surgery for its potential complications and postoperative demanding rehabilitation protocol. We aimed to describe the surgical technique for microfracturing osteochondral lesions of the femoral head with a 3.2-mm drill in an arthroscopically assisted manner and to describe the outcome of this procedure. We describe 9 transtrochanteric drillings throughout an otherwise uneventful arthroscopic treatment of femoroacetabular impingement pathology. All of them had a parafoveal osteochondral lesion unapproachable with curved awls through routinely used portals. After debriding the cartilage flap with a chondrotome, the surgical technique consisted of a minimally invasive 3.2-mm drilling through the femoral lateral cortex fluoroscopically guided. Mean follow-up was 55.8 months (range, 43 to 113 mo). Outcome was evaluated with the modified Harris Hip Score (mHHS) and healing was assessed through magnetic resonance imaging findings. Overall, all patients showed better results when comparing preoperative and postoperative mHHS (43.8 vs. 79.5; P = 0.0008). No complications were reported due to the surgical technique. Complete healing of the osteochondral lesion was confirmed in 7 of 9 cases, and partially in one. One patient with Tönnis 2 preoperative changes required conversion to total hip arthroplasty at 80-month followup. Retrograde drilling was a valid option for treating small-sized medially located osteochondral lesions of the femoral head which are difficult to treat through standard arthroscopic portals.