The New York Yankees selected Eiland in the seventh round of the 1987 MLB draft and he made his major league pitching debut with the Yankees in August 1988. Used mainly in spot chances, Eiland pitched in New York for four seasons, winning five games. He was traded to the Padres in 1992 and did not win a game in two seasons despite starting in nine games. Eiland was sent back to the Yankees in 1995 and played for the expansion Devil Rays for three seasons before retiring in 2000. He played for 10 seasons, with 12 wins and 27 losses and a career ERA of 5.74.