In a November 7, 2018, game against the Penguins, Oshie was injured twice on the ice and came back to score the winning goal with 1:14 minutes left in the game. Oshie was sent to the training room twice, the first time requiring two stitches to a cut near his left eye created by an opponent's stick. He then took an shoulder check to the head from Evgeni Malkin. On November 14, in a 3–1 loss to the Winnipeg Jets, Oshie suffered a possible concussion when he was slammed down by the Jets' defenseman Josh Morrissey, who was later fined for unsportsmanlike conduct. Oshie has four reported concussions in his NHL career. After missing 11 games, he returned for a December 11, 2018 home game against the Detroit Red Wings, scoring a goal in the 6-2 Caps win.