Intracranial hypotension can be a common sequela of a cerebrospinal fluid (CSF) leak. However, evidence of such a condition related to an injury in American football is currently lacking in the literature. While a positional or orthostatic headache is the most classic symptom of headaches due to intracranial hypotension, a variety of nonspecific symptoms such as neck pain, nausea, vomiting, photophobia, phonophobia, and visual changes can also be present. We present two cases where collegiate American football players developed protracted headaches after a concussive injury and were subsequently diagnosed with intracranial hypotension thought secondary to spinal CSF leaks. Both players underwent multiple procedures of fluoroscopic-guided autologous blood patching, with improvement in their headaches. Recovery varied between the athletes. Case 1 achieved full resolution of his headaches and returned to full activity. Case 2 continued to have intermittent headaches after blood patching, but the positional nature had resolved and he was cleared for full participation in football and was closely followed during the remainder of his collegiate career. Both these cases emphasize the importance of including CSF leak as a cause of post-traumatic headache in an American football player.