Morel-Lavallee lesions (MLL) are rare, closed degloving injuries caused by trauma that delivers a shearing force to the soft tissue most commonly of the hip. If not treated in the acute and subacute setting these lesions are often complicated by re-accumulation of fluid, infection, or chronic pain. We present a unique case of a recurrent, massive medial knee/thigh MLL in which proper treatment was delayed due to initial diagnosis of a quadriceps contusion. We describe the ultrasound and magnetic resonance imaging findings of this patient and based on a review of recent literature propose that the initial management should have included early drainage/debridement, which likely could have prevented recurrence and significantly shortened the clinical course.