The diagnosis of an intra-articular osteoid osteoma can be a challenging and lengthy process, with reports of delayed diagnosis of greater than 2 years. In the young, athletic patient with an atraumatic onset of groin pain, an overuse injury or muscle strain is the most likely etiology. However, an overuse injury of femoral neck stress fracture must be identified because of the potentially disastrous outcome of fracture completion. The similar clinical presentation of a femoral neck stress fracture and intra-articular osteoid osteoma of the femoral neck can further delay the diagnosis of the osteoid osteoma. In a patient with these differential diagnoses that do not improve with a period of nonweightbearing activity, a more intensive workup must ensue. The purpose of this case report is to describe the initial presentations, subsequent follow-up, and imaging findings leading to the diagnosis of osteoid osteoma as well as to differentiate an osteoid osteoma from femoral neck stress injuries.