On November 24, 1998, Alomar signed a four-year contract with the Cleveland Indians, joining his All-Star brother, Sandy Jr. It was in Cleveland that Alomar had two of his finest seasons. In 1999, he hit .323 and set career highs with 24 home runs, 120 RBI, 138 runs, 99 walks, a .422 on-base percentage and a .533 slugging percentage. In 2001, he batted .336/.415/.541, with 20 home runs, 100 RBI, and 30 steals. Cleveland made the playoffs in 1999, losing in the ALDS to the Boston Red Sox; in 2001, they again made the playoffs, but lost to the Seattle Mariners in the ALDS. Alomar finished third in AL MVP voting in 1999 and fourth in 2001.