Metastases from prostate cancer occur largely in bone through a haematogenous route. Metastatic spread of prostate cancer to the leptomeninges was rarely seen in the past. However, there has been a recent increase in presentations of leptomeningeal spread from prostate cancer in our institutions. Between 2004 and 2006, four patients were diagnosed with metastatic prostate cancer with leptomeningeal metastases in our centres. All four patients had hormone refractory prostate cancer and had previously had chemotherapy. The median survival of these patients was approximately 15 months from the time of hormone refractoriness. The prognosis of leptomeningeal metastasis secondary to metastatic prostate cancer is poor, ranging from 2 to 7 months as seen in our series. New cases of leptomeningeal metastases seen in our series are hypothesized to be secondary to the use of effective modern systemic treatments. A parallel might be drawn with the increased rate of central nervous system metastases in breast cancer since the introduction of effective cytotoxic treatments and more recently targeted therapies. We suggest the clinicians to be aware of the potential change of natural history and pattern of progression in metastatic prostate cancer.