Introduction: There is a paucity of data investigating the relationship between histopathological variables of oncologic importance and prostate volume, and we aimed to investigate this. Patients and Methods: 2,207 consecutive patients who underwent robotic-assisted radical prostatectomy were studied. Preoperative demographic and both pre- and postoperative histopathological parameters were compared among the small (<40 cm3), intermediate (40–70 cm3), and large (>70 cm3) prostate groups. Results: Patients with smaller prostates were younger, had slightly lower BMIs, and lower prostate-specific antigen (PSA) levels than those with larger prostates (p < 0.001). They also had worse histopathological criteria (Gleason, core positivity, and maximum percent cancer) on preoperative biopsy and had worse radical specimen Gleason sums (p < 0.001), percent cancer (p < 0.001), and pathological stage (p = 0.016). 11.5% of the men in the small prostate group suffered a positive surgical margin (PSM) compared to 8.3 and 5.6% in the intermediate and large prostate groups, respectively (p = 0.008). Basilar, posterolateral, and multifocal PSMs were commoner in the small prostate group. Conclusions: Younger men have smaller prostates and worse preoperative histopathological parameters despite lower PSA values. Men with small prostates undergoing robotic-assisted radical prostatectomy have worse final Gleason sums, tumour volume, extraprostatic extension, and PSM rates than those with larger prostates.