The ideal management of cryptorchidism is a highly debated topic within the field of pediatric surgery. The optimal timing of orchiopexy is particularly unclear, as existing literature reports mixed recommendations. The aim of this study was to determine, based on a systematic review, the most favorable age at which orchiopexy should be performed. We conducted a systematic search of MEDLINE, Embase, CINAHL, and the Cochrane Library to find relevant articles. Two researchers quality assessed each study using the following tools: AMSTAR (systematic reviews), Jadad (RCTs), and MINORS (non-RCTs). We developed a conclusion based on the highest quality studies. We found one relevant systematic review, one RCT, and 30 non-RCTs. Fertility potential was greatest when orchiopexy was performed before 1 year of age. Additionally, orchiopexy before 10–11 years may protect against the increased risk of testicular cancer associated with cryptorchidism. Orchiopexy should not be performed before 6 months of age, as testes may descend spontaneously during the first few months of life. The highest quality evidence recommends orchiopexy between 6 and 12 months of age. Surgery during this timeframe may optimize fertility potential and protect against testicular malignancy in children with cryptorchidism.