Background: Evidence on return to sport (RTS) criteria and timelines for pediatric patients with osteochondral (OCD) lesions of the foot and ankle is limited. Methods: This systematic review evaluated RTS criteria and outcomes in this population by querying PubMed, Embase, Web of Science, CINAHL, and SPORTDiscus up to 30 May 2024. Inclusion criteria were retrospective or prospective studies that examined pediatric patients with osteochondral lesions of the foot and ankle and gave outcomes or criteria regarding RTS. Results: Five observational studies (n = 168 patients; n = 180 OCD lesions; mean age: 14.19 ± 0.47 years; mean follow-up: 42 ± 174 months) were included. Two studies (40%) used time-based criteria for RTS, two studies (40%) used mixed criteria, and the final study (20%) used milestone-based criteria. Across the mixed and milestone criteria, physical therapy (n = 3) and minimal partial weight-bearing prior to RTS (n = 4) were most frequently seen as the milestones used for assessing RTS readiness. RTS from the postoperative period ranged from 3 months to 6 months. At the final follow-up, 61.45% of patients (n = 110) were available to provide information regarding their ability to RTS. Of these patients, 80% (n = 88) achieved RTS. Conclusions: Results showed variability in RTS criteria, ranging from three to six months, with no clear patterns. Most patients returned to sport, suggesting that such individualized criteria may be effective to an extent. Future research should focus on larger, high-quality studies to develop consistent RTS protocols.