Background: Chronic constipation, a prevalent gastrointestinal complaint, exhibits rising incidence and diverse clinical implications, especially among the aging population. This study aims to assess colonoscopy performance in chronic constipation across age groups, comprehensively evaluating diagnostic yield and comparing results with average-risk controls. Methods: A retrospective analysis was conducted on 50,578 colonoscopy procedures performed over 12 years, including 5478 constipated patients. An average-risk control group (n = 4100) was included. Data extracted from electronic medical records covered demographics, operational aspects, and colonoscopy findings. The primary outcome measures included the diagnosis rate of colorectal cancer (CRC), polyp detection rate (PDR), and inflammatory bowel disease (IBD) diagnoses in constipated patients versus controls, with age-based and multivariate analyses. Results: Constipated patients exhibiting lower rates of adequate bowel preparation (92.7% vs. 85.3%; p < 0.001) and a lower cecal intubation rate. No significant variances between CRC and PDR were observed between constipated and controls, except for a potential of a slightly elevated CRC risk in constipated patients older than 80 (2.50% vs. 0% in controls; p = 0.07). Multivariate analysis demonstrated, across all age groups, that constipation did not confer an increased risk for CRC or polyp detection. Younger constipated patients exhibited a higher rate of IBD diagnoses (1.7% vs. 0.1% in controls; p < 0.001). Conclusions: Constipation did not confer an increased risk for CRC or polyps, among any age groups, except for a potential signal of elevated CRC risk in patients older than 80; additionally, it was associated with higher rates of IBD in younger patients.