Before the 1988 season, the Padres traded Gossage and Ray Hayward to the Cubs for Keith Moreland and Mike Brumley. On August 6, , while with the Cubs, Gossage became the second pitcher to record 300 career saves in a 7–4 victory over the Philadelphia Phillies, coming into the game with two out in the ninth and two men on base and retiring Phil Bradley on a popup to second baseman Ryne Sandberg. Released by the Cubs in March 1989, he signed with the San Francisco Giants in April. The Yankees selected Gossage off of waivers in August. He pitched for the Fukuoka Daiei Hawks of Nippon Professional Baseball in 1990.