Background: A postoperative discal/annular cyst following lumbar discectomy may reproduce the symptoms/signs of a recurrent lumbar disc herniation (i.e., back pain and radiculopathy). Case Description: A 21-year-old rugby player developed leg pain after an uncomplicated lumbar microdiscectomy. The repeat lumbar magnetic resonance imaging confirmed a postoperative lumbar annular/ discal cyst, for which he underwent repeat surgery. The diagnosis was further confirmed histopathologically at surgery. Conclusion: Although rare, postoperative discal/annular cysts may be potential causes of recurrent postoperative pain and lumbar radiculopathy mimicking recurrent disc herniations.