[2] In 1986, he transferred to the University of South Florida in Tampa and finished his collegiate career playing for the Bulls baseball team.

[4] He was fast-tracked through the system, starting the 1988 season at Double-A Albany before getting called up to Triple-A Columbus in July.

[5] He allowed three hits in seven innings, including a home run to the first batter he faced, Paul Molitor.

Unhappy with the decision, he told the media "it was a stupid move on the part of the Yankees and I'm looking forward to leaving.

[12][13][8] On April 10, he hit a home run in his first plate appearance, facing Bob Ojeda of the Los Angeles Dodgers.

[6] Eiland re-signed with the Yankees for the 1995 season and was finally recalled on July 19 to make a spot start.

[21] On December 6, 1995, Eiland signed a minor league deal with the St. Louis Cardinals and started the season in Triple-A.

[29] Eiland considered retiring at the end of the 1997 season before signing a minor league deal with the Tampa Bay Devil Rays in December 1997.

He missed the entire 2001 season after undergoing Tommy John surgery, and then re-tore the ligament in April 2002.

[41][42] During his tenure in the Yankees farm system, Eiland oversaw the development of prospects including Phil Hughes,[43] Joba Chamberlain,[44] and Ian Kennedy.

[58] After the 2010 season, Eiland joined the Tampa Bay Rays as a special assistant to general manager Andrew Friedman.

[63] When the Mets named Mickey Callaway as their manager after the 2017 season, Eiland was hired as the team's pitching coach.

[64] He worked with Jacob deGrom to simplify his approach, helping him win the Cy Young Award in 2018 and 2019.

[66] He helped Zack Wheeler change his mechanics in order to improve his timing and increase his velocity.

[69] On March 2, 2021, Eiland was named pitching coach for the Lexington Legends of the Atlantic League of Professional Baseball.

[70][71] In 2022, Eiland was hired by the Miami Marlins organization to be the pitching coach for the Pensacola Blue Wahoos in Double-A.

[74] During his time with the Devil Rays, Eiland acted as a body double for Kevin Costner, who played a starting pitcher and run scorer in the 1999 film For Love of the Game.