Background: Pediatric polypharmacy is increasingly recognized among children with chronic medical conditions; however, data from outpatient settings, particularly in the Middle East, remain limited. This study aimed to determine the prevalence, patterns, and factors associated with pediatric polypharmacy among outpatients at a tertiary care hospital. Methods: We conducted a retrospective cross-sectional study of pediatric outpatients (<18 years) with at least one recorded prescription attending a tertiary hospital between October 2024 and October 2025. Polypharmacy was defined as the concurrent use of five or more eligible prescribed medications for at least 30 consecutive days. Oral, inhaled, and injectable medications were included, whereas PRN, topical, ophthalmic, otic, intranasal, and routine nutritional supplements were excluded. Therapeutic folic acid, iron, calcium supplements, and pyridoxine were retained when prescribed for specific clinical indications. Descriptive statistics, univariable analyses, Spearman correlation, and multivariable logistic regression were performed. Results: Among 6578 pediatric outpatients, 82 met the study definition of polypharmacy, yielding a prevalence of 1.2% (95% CI: 1.01–1.54%). Children with polypharmacy were significantly older and had greater outpatient, inpatient, emergency department, and total healthcare utilization than those without polypharmacy. Multivariable logistic regression identified older age (OR 1.136, 95% CI 1.076–1.199; p < 0.001) and outpatient visit frequency (OR 1.350, 95% CI 1.288–1.417; p < 0.001) as factors independently associated with polypharmacy, whereas sex, inpatient visits, and emergency visits were not independently associated. Epilepsy was the most common diagnosis, followed by bronchial asthma and chronic kidney disease. Pantoprazole was the most frequently prescribed medication, while endocrinology and rheumatology were the most frequently attended specialties. Conclusions: Using a definition requiring sustained concurrent medication use, pediatric polypharmacy was uncommon in this outpatient population but was independently associated with older age and greater outpatient healthcare utilization. These findings support targeted medication review and optimization strategies for children with chronic diseases requiring frequent outpatient follow-up and provide baseline data for pediatric medication safety initiatives.