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Background Various reports suggested that pre-existing medical illnesses, including hypertension and other demographic, clinical, and laboratory factors, could pose an increased risk of disease severity and mortality among COVID-19 patients. This study aimed to assess the relation of hypertension and other factors to the severity of COVID-19 pneumonia in patients discharged from Eka Kotebe Hospital in June-September, 2020. Methods This is a single-center case-control study of 265 adult patients discharged alive or dead, 75 with a course of severe COVID-19 for the cases arm and 190 with the non-severe disease for the control arm. Three age and sex-matched controls were selected randomly for each patient on the case arm. Chi-square, multivariable binary logistic regression, and odds ratio (OR) with a 95% confidence interval was used to assess the association between the various factors and the severity of the disease. A p-value of Results Of the 265 study participants, 80% were male. The median age was 43 IQR(36–60) years. Both arms had similar demographic characteristics. Hypertension was strongly associated with the severity of COVID-19 pneumonia based on effect outcome adjustment (AOR = 2.93, 95% CI 1.489, 5.783, p-value = 0.002), similarly, having diabetes mellitus (AOR = 3.17, 95% CI 1.374, 7.313, p-value Conclusions Hypertension was associated with the severity of COVID-19 pneumonia, and so were diabetes mellitus, chronic cardiac disease, and an increase in pulse rate.