Background and Objectives: Urinary tract infections (UTIs) are an important cause of perinatal and maternal morbidity and mortality. The aim of this study was to describe and compare the main pregnancy outcomes among pregnant patients with complicated and uncomplicated UTIs; Materials and Methods: This retrospective study included 183 pregnant patients who were evaluated for uncomplicated UTIs and urosepsis in the Urology Department of ‘C.I. Parhon’ University Hospital, and who were followed up at a tertiary maternity hospital—‘Cuza-voda’ from Romania between January 2014 and October 2023. The control group (183 patients) was randomly selected from the patient’s cohort who gave birth in the same time frame at the maternity hospital without urinary pathology. Clinical and paraclinical data were examined. Descriptive statistics and a conditional logistic regression model were used to analyze our data. Results: Our results indicated that patients with urosepsis had increased risk of premature rupture of membranes (aOR: 5.59, 95%CI: 2.02–15.40, p < 0.001) and preterm birth (aOR: 2.47, 95%CI: 1.15–5.33, p = 0.02). We could not demonstrate a statistically significant association between intrauterine growth restriction and pre-eclampsia with the studied urological pathologies. Conclusions: Careful UTI screening during pregnancy is needed for preventing maternal–fetal complications.