Background This study aimed, first, to angiographically investigate and analyze prostatic artery (PA) origin in a Greek male population with benign prostatic hyperplasia (BPH) treated with prostatic artery embolization (PAE) and, second, to correlate prostatic arterial anatomy with technical and clinical aspects of PAE. Methodology This was a retrospective study of BPH patients who underwent PAE in a single tertiary center in Greece from June 2019 to July 2022. For the first part of the study, PA was imaged with computed tomography angiography (CTA) before PAE and with digital subtraction angiography (DSA) during PAE in all patients. A widely accepted system for the classification of PA origin was applied. Type I, a common origin of PA and superior vesical artery (SVA) from the anterior division of internal iliac artery (IIA). Type II, PA originating from the anterior division of IIA, separate from, and inferior to SVA. Type III, the origin of PA from the obturator artery. Type IV, the origin of PA from the internal pudendal artery. Type V, rarer origins of PA. For the second part of the study, a subgroup of patients from the first part (treated with the same PAE protocol and free of vascular pathology that could have interfered with the technical success of PAE) was selected. In this subgroup, differences in PA origin were correlated with technical aspects (feasibility of catheterization of PA, fluoroscopy time (FT), dose area product (DAP)) and clinical outcomes of PAE. Results After the exclusion of four patients, 159 patients were included in the first part of the study. From a total of 355 PAs, 110 (31%) were compatible with type I, 58 (16.3%) type II, 45 (12.7%) type III, 110 (31%) type IV, and 32 (9%) type V. PA origin from an accessory internal pudendal artery was the most common among the rare origins of type V. Regarding the second part of the study (a subgroup of 101 patients selected to facilitate comparisons between the different types of PA origin), type I was associated with significantly more incidences of failed or difficult catheterization of the PA compared to all other types combined (27/64 vs. 18/138, p < 0.001). Types III, IV, and V showed a relatively low degree of technical difficulty. Patients with type I PA origin of at least one pelvic side (subgroup (I), n = 48) had significantly longer FT and DAP compared to the rest (subgroup (O), n = 53). Clinical success rates of PAE were slightly lower for the subgroup (I), although the difference was not statistically significant (75.8% vs. 83.8% at 18 months post-PAE, p = 0.137). No major complications were observed. Conclusions This is the first study of PA origin in Greece. It was demonstrated that types I and IV of PA origin were the most common and had the same prevalence. Type I showed significantly higher technical difficulty compared to the others, but had no significant impact on the clinical outcomes of PAE.