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Although prostate cancer is notable for its high incidence and mortality in men worldwide, its identification remains a challenge. Biomarkers have been useful tools for the specific detection of prostate cancer. Unfortunately, benign prostate diseases cause similar alterations in screening assays thus reducing the potential for early and specific diagnosis. Changes in glycan and glycoprotein expression have often been associated with the onset and progression of cancer. Abnormal glycans and glycoproteins have been reported as new biomarkers of prostate metabolism that can distinguish benign prostate disease and cancer in non-aggressive and aggressive stages. Carbohydrate-binding proteins known as lectins have been valuable tools to detect these changes, investigate potential biomarkers and improve our understanding aberrant glycosylation in cancer. Here we review progress in elucidating prostate disease and discuss the roles of glycans in the differential detection of benign and cancerous prostate disease. We also summarize the lectin-based tools for detecting glycosylation changes.