Before the 1999 season, Lawton in the Twins failed to agree on a contract. This led to arbitration proceedings, with Lawton requesting US$2.4 million. The Twins countered with a US$1.7 million contract, which Lawton refused. On April 18, 1999, Lawton hit a grand slam in the bottom of the 11 inning to give the Twins the victory over the Cleveland Indians. Todd Walker, the Twins infielder at the time, was Lawton's good friend since they met in the minors. On June 8, Lawton shattered his eye socket in two places after being hit by a pitch from Cincinnati Reds pitcher Dennys Reyes. Lawton played five rehab games in the minor leagues with the rookie-level Gulf Coast League Twins, and the Class-A Advanced Fort Myers Miracle, batting a combined .500. Lawton made his return to the majors on July 18. He wore a protective cage on his batting helmet until July 21, shedding it because it limited his vision. During a game at the SkyDome against the Toronto Blue Jays, Lawton spat towards a 16-year-old fan who called him a racial slur. The two later exchanged apologies. Lawton potentially faced assault charges, but nothing was ever filed. On the season, Lawton batted .259 with 58 runs scored, 105 hits, 18 doubles, seven home runs, 54 RBIs, and 26 stolen bases in 118 games played. In the field, he played 103 games in right field, 10 in left field, and six in center field. In all of his outfield games, Lawton committed four errors; and made three assists and 231 putouts.