In his first season in the American League, Raines hit for a .268 average but with a .359 on-base percentage; he was second on the team in runs scored as the White Sox finished the season in second place in the American League Western Division. His average improved in 1992 to .294 with a .380 on-base percentage. In 1993, despite missing nearly six weeks in April and May due to a torn ligament in his thumb he suffered while stealing a base, he managed to hit .306 with 16 home runs as the White Sox won the American League Western Division title. In the 1993 American League Championship Series against the Toronto Blue Jays, Raines posted a .444 batting average and scored five runs in a losing cause.