<b><i>Background:</i></b> Recent years have witnessed a huge shift in the management and prognosis of metastatic prostate cancer with the advent of new-generation anti-hormonal treatments. Docetaxel, which was initially approved in the castrate-resistant prostate cancer setting, has been approved in the earlier course of the disease as it is still castrate sensitive. <b><i>Summary:</i></b> Apart from cabazitaxel and in the absence of other effective chemotherapies, docetaxel rechallenge (DR) in patients with proved sensitivity to docetaxel in the earlier stage of the disease remains a possible option. Unfortunately, the pivotal trials rarely reported on the outcomes of docetaxel retreatment which seems a plausible option in patients initially responding to docetaxel and maintaining a minimum progression-free interval of 3–6 months. In this review, a summary of the clinical evidence and potential concerns for the use of DR in patients with metastatic prostate cancer will be presented. <b><i>Key Messages:</i></b> Pivotal trials of docetaxel in metastatic castrate-sensitive prostate cancer as well as metastatic castrate-resistant prostate cancer have not reported on the outcomes of DR except in the GETUG-AFU 15 trial where the outcomes were disappointing. Based on the published retrospective data, DR may be effective in patients who initially responded to docetaxel and maintained a progression-free interval exceeding 6 months.