Although the shoulder is one of the most commonly dislocated joints in the body, bilateral gleno-humeral joint dislocation is considered rare. Due to its complexity and paucity of cases reported in the literature, it represents both a diagnostic and therapeutic challenge. We report a rare case of an adolescent boy who suffered chronic bilateral anterior shoulder dislocations with proximal humerus fracture and Hill-Sachs lesion after febrile seizure following COVID-19 vaccination. An 18-year-old male presented with bilateral proximal humerus fracture with anterior shoulder dislocation following a first-time seizure. He was managed with a bilateral Latarjet procedure and proximal humerus interlocking osteosynthesis (PHILOS) on the left side, and the right-side fracture was fixed with two 3.5 mm cannulated screws. After one year, the patient had a somewhat satisfactory outcome with a DASH (disabilities of the arm, shoulder, and hand) score of 31.8. Bilateral anterior shoulder dislocation with associated proximal humerus fracture remains one of the rare orthopedic injuries. Recurrent shoulder dislocations lead to chronic glenoid bone loss, which needs fixation along with fracture.