Background: Microsurgical removal represents a well-accepted treatment option for symptomatic benign pineal cysts (PCs). However, very few studies have quantitatively evaluated the functional status of surgically treated PC patients. Methods: A detailed analysis of preoperative, immediate postoperative, and long-term clinical and radiological characteristics was performed. The functional status of the patients was categorized using the modified Rankin scale (MRS) and the Chicago Chiari Outcome Scale (CCOS). In addition, a comparative analysis between pediatric and adult patients with PCs was carried out. Results: Overall, pediatric patients experienced better long-term MRS scores than adults. The differences between the pre-, the immediate post-, and the last postoperative MRS of the patients were statistically significant for the total population (P < 0.001). All patients obtained a CCOS of 11 or more, which reflects a good/optimal result after microneurosurgery. The type of the surgical approach was independently associated with the postoperative complications (P < 0.01), more frequently reported with the midline supracerebellar infratentorial (SCIT) approach than with its paramedian modification. Conclusion: The functional status of properly selected symptomatic patients with PCs may improve significantly after their surgical management through a paramedian SCIT approach in sitting position.