We compared subtotal meniscectomy and saucerization with stabilization for osteocartilaginous damage based on injured location and further examined the factors related to osteocartilaginous damage in juvenile discoid lateral meniscus (DLM) with peripheral tear after a follow-up period of at least 5years. We retrospectively reviewed juvenile DLM patients with peripheral tear who underwent arthroscopic surgery with more than 5years of follow-up. Osteocartilaginous damage, which was identified by osteochondritis dissecans (OCD) development and the whole-organ magnetic resonance imaging score (WORMS) of cartilage grade ≥ 3, was compared between subtotal meniscectomy and saucerization with stabilization. A subgroup analysis examining the location of the tear site was performed. Factors for osteocartilaginous damage were analyzed between the damaged and non-damaged groups. Forty-one patients, including 29 who underwent saucerization with stabilization and 12 who underwent subtotal meniscectomy, were included in this study. Seven patients developed OCD lesions; six patients showed cartilage WORMS of more than grade 3. Overall, there was a significant difference in the total cartilage and meniscus WORMS between the two groups at the final follow-up. The subgroup analysis demonstrated more severe osteocartilaginous damage developed in posterior subtotal meniscectomy than in posterior stabilization following saucerization. The damaged group showed significant difference compared to the non-damaged group in terms of age (p = 0.003), sex (p = 0.036), and posterior subtotal meniscectomy (p < 0.001). Posterior subtotal meniscectomy revealed the worst scenario for the progression of osteocartilaginous damage in cases of juvenile DLM with peripheral tear over a minimum follow-up period of 5years.