before the Southern League All-Star Game and played in the game wearing an Indians hat even though the Indians did not have a Southern League team at the time. He was assigned to the Akron Aeros of the Eastern League, where he batted .361 in 56 games with 28 steals. He was promoted to the Buffalo Bisons, the Indians' Triple-A team in the International League, late in the season. He had only two hits in 15 at-bats for the Bisons but remained with the team in the playoffs, as the Bisons won their first Governors' Cup in nearly 40 years and made it to the Triple-A World Series. Roberts later said his promotion to Buffalo was exciting because he realized he was getting close to the big leagues and his time there made him a better player. Roberts played with the Cañeros de Los Mochis of the Mexican Pacific League during the 1998–99 season before playing for the Criollos de Caguas in Puerto Rico, where he played with Alex Cora, and had Joey Cora as general manager. Almost 20 years later Roberts, as manager of the Dodgers, would go on to meet Alex Cora as manager of the Red Sox in the 2018 MLB World Series. Roberts was a non-roster invitee at Indians spring training in 1999 but was assigned to Buffalo to start the season. In 89 games for the Bisons, he had a .271 batting average with 39 steals. He earned International League all-star honors for the season. His contract was purchased by the Indians on August 7, 1999 and he made his major league debut batting leadoff and playing center field for the Indians against the Tampa Bay Devil Rays. In his debut he had three hits in five at-bats and stole a base: he was also picked off once. His first MLB hit was a double to center field in his second at-bat, off of Bobby Witt of the Devil Rays in the second inning. He hit his first home run on August 30 off of Ramón Ortiz of the Anaheim Angels. On September 24, he hit a grand slam homer off of John Hudek of the Toronto Blue Jays. Overall, he was in 41 games for the Indians in 1999 and hit .238 with two homers, 12 RBI and 11 stolen bases. He also appeared in two games of the 1999 American League Division Series