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Background: The International Society of Urological Pathology (ISUP) grade and positive surgical margins (PSMs) after radical prostatectomy (RP) may reflect the prognosis of prostate cancer (PCa) patients. This study aimed to investigate whether DCE-MRI parameters (i.e., <i>K^trans</i>, <i>k_ep</i>, and IAUC) could predict ISUP grade and PSMs after RP. Method: Forty-five PCa patients underwent preoperative DCE-MRI. The clinical characteristics and DCE-MRI parameters of the 45 patients were compared between the low- and high-risk (i.e., ISUP grades III-V) groups and between patients with or without PSMs after RP. Multivariate logistic regression analysis was used to identify the significant predictors of placement in the high-risk group and PSMs. Results: The DCE parameter <i>K^trans-max</i> was significantly higher in the high-risk group than in the low-risk group (<i>p</i> = 0.028) and was also a significant predictor of placement in the high-risk group (odds ratio [OR] = 1.032, 95% confidence interval [CI] = 1.005–1.060, <i>p</i> = 0.021). Patients with PSMs had significantly higher prostate-specific antigen (PSA) titers, positive biopsy core percentages, <i>K^trans-max</i>, <i>k_ep-median</i>, and <i>k_ep-max</i> than others (all <i>p</i> < 0.05). Of these, positive biopsy core percentage (OR = 1.035, 95% CI = 1.003–1.068, <i>p</i> = 0.032) and <i>k_ep-ma</i>_x (OR = 1.078, 95% CI = 1.012–1.148, <i>p</i> = 0.020) were significant predictors of PSMs. Conclusion: Preoperative DCE-MRI parameters, specifically <i>K^trans-max</i> and <i>k_ep-max,</i> could potentially serve as preoperative imaging biomarkers for postoperative PCa prognosis based on their predictability of PCa risk group and PSM on RP, respectively.