Background: The study aimed to estimate the duration of viral shedding (DVS) in patients with confirmed coronavirus disease 2019 (COVID-19), investigated the factors affecting that duration, and identified the redetectable positive (RP) cases in the recovered COVID-19 patients in Prince Sultan Military Medical City (PSMMC). Methods: The study was a retrospective record base design in the PSMMC that included 171 confirmed COVID-19 patients from 15 March to 31 May 2020. Their clinical characteristics and laboratory findings were retrieved and reviewed based on the PSMMC COVID-19 database and the Ministry of Health (MOH) Health Electronic Surveillance Network. Data analysis used the SPSS software package to measure the DVS, explore its potential factors, and identify the RP cases. The data presented as frequency distribution tables, medians, and interquartile range (IQR). Mann–Whitney U and Kruskal–Wallis tests compared the medians to explore the significant variables that affect DVS. Results: The median DVS was 11 days, IQR was 7 to 15 days, and statistically significant longer the patient presented with fever (P = 0.025), among health care workers (HCWs) (P = 0.020), and the age group above 65 (P = 0.039). Overall, 13 patients (7.6%) were RP, statistically significantly higher among the contacts to confirmed COVID-19 cases. Conclusions: The DVS in PSMMC COVID-19 patients is comparable to the isolation period approved by MOH. Fever was a risk factor for a prolonged DVS, advised an extended follow-up period for these patients. RP cases were significantly higher among the contacts to COVID-19 cases than non-contacts. The study suggests future comprehensive research on the RP characteristics.