Urinary tract infections (UTIs) are the third most common types of infection in human medicine worldwide. There is increasing appreciation for the pathogenic role of Gram-positive cocci (GPC) in UTIs, as they have a plethora of virulence factors, maintaining their pathogenicity and high affinity for the epithelial cells of the urinary tract. The study was carried out using microbiological data collected corresponding to the period between 2008 and 2017. Antimicrobial susceptibility testing was performed using the disk diffusion method and E-tests. The age range of patients affected from the outpatient and inpatient groups differed significantly (43 [range 0.7–99] vs. 68 [range 0.4–99] years; p = 0.008). 3962 GPCs were obtained from inpatient and 4358 from outpatient samples, corresponding to 20.5 ± 2.8% (range 17.5–26.8%) and 20.6 ± 2.6% (range 17.8–26.0%) of all positive urine samples (p > 0.05); in both groups, Enterococcus spp. were the most prevalent (outpatients: 79.6%; inpatients: 88.5%). High-level aminoglycoside resistance in enterococci was noted in 31.0–46.6% of cases. A pronounced increase in the number of MRSA was seen in the second half of the study period (0.6–1.9% vs. 9.8–11.6%; p = 0.038). The ratio of VRE isolates was 0.16%, no VISA/VRSA isolates were detected.