All Out War
He is seen offering food to Maggie and Andrea as they sit at the steps of the Hilltop mansion. As The Saviors infiltrate the Hilltop's wall, he hides in the Hilltop mansion.
Whispers Into Screams
Oscar is seen watching Maggie braking in a horse, and is asked by Maggie to take her back to the stables. Later, when Paul Monroe rides into the Hilltop Colony with an injured Darius, yelling for Carson, Oscar comes running, along with Earl Sutton, and helps Darius off the horse and takes him to Doctor Carson. When Carl appears with an injured Sophia who was beaten by two bullies, he helps Maggie carry her to the medical facility.