Our aim was to investigate which features were associated with clinical successes at short- and mid-terms following prostate artery embolization (PAE) for symptomatic benign prostate hypertrophy (BPH). All adults treated by PAE for BPH at our referral center between January 2017 and March 2021, with pre-treatment MRI, technical success, and follow-up at 3 months and 2 years were included in this single-center retrospective study. Radiologists reviewed the prostatic protrusion index (PPI), adenomatous dominant BPH (adBPH), and Wasserman classification on pre-treatment MRI. Radiomics analysis was achieved on the transitional zone on pre-treatment T2-weighted imaging (WI) and ADC, and comprised reproducibility assessment, unsupervised classifications, and supervised radiomics scores obtained with cross-validated Elasticnet regressions. Eighty-eight patients were included (median age: 65 years), with 81.8% clinical successes at 3 months and 60.2% at 2 years. No feature was associated with success at 3 months, except the radiomics score trained on T2-WI and ADC (AUROC = 0.694). Regarding success at 2 years, no radiomics approaches provided significant performances; however, Wasserman type-1 and change in international prostate symptom score (IPSS) at 3 months ≤ −35% were associated with success in multivariable analysis (OR = 5.82, p = 0.0296, and OR = 9.04, p = 0.0002). Thus, while radiomics provided limited interest, Wasserman classification and early IPSS changes appeared predictive of mid-term outcomes.