Purpose: To assess the effectiveness of cadaveric ankle arthroscopy courses in reducing iatrogenic injuries. Methods: A total of 60 novice surgeons enrolled in a basic cadaveric ankle arthroscopy course were divided into two groups. Group A (n = 32) was lectured on portal placement and use of the arthroscope, whereas group B (n = 28) was in addition lectured on specific portal-related complications. Following the performance of anterior ankle arthroscopy and hindfoot endoscopy, the specimens were dissected and carefully assessed for detection of any iatrogenic injuries. Results: The rate of injury to the superficial peroneal nerve (SPN) was reduced from 25 to 3.6%, in group A compared with B (p = 0.033). Injuries to the peroneus tertius or extensor digitorum longus, the flexor hallucis longus and the tibial nerve or the Achilles tendon were also reduced in group B. Overall, the number of uninjured specimens was 50% (n = 30) and higher in group B (57%) than group A (44%). Lesions to the plantaris tendon, the sural nerve or the posterior tibial artery were more common in group B, however, without reaching statistical significance. Overall, 25 (13.9%) anatomic structures were injured in anterior arthroscopy compared to 18 (5%) in hindfoot endoscopy, out of a potential total of 180 and 360, respectively (p = 0.001). Conclusion: Dedicated lectures on portal-related complications have proven useful in reducing the risk of injury to the SPN, the commonest iatrogenic injury encountered in ankle arthroscopy. Hindfoot endoscopy is significantly safer than anterior ankle arthroscopy in terms of injury to anatomical structures.