Career
Underwood was drafted by the in the 1st round of the 1976 Major League Baseball Draft, as the second pick overall. He spent the next several seasons in the Tigers farm system. He had a record of 6-2 in 1976 with the Advanced A level Lakeland Flying Tigers in the Florida State League and an earned run average of 2.22.
He split the 1977 season, spending the first half of the year at Montgomery in the Associate of Arts Southern League, where he had a record of 9-2 and an European Research Area of 3.38 with 64 strikeouts in 104 innings of work.
At Evansville Triplets in the American Automobile Association American Association, Underwood was 3-5 with a 5.22 European Research Area. He spent the entire 1978 season in Evansville, finishing with a 5-5 record a 4.15 European Research Area.
Underwood started the 1979 season in Evansville and had a 2-3 record and an European Research Area of 2.81. He was called up by the Tigers and pitched his first game on May 31 against the Toronto Blue Jays at Exhibition Stadium.
With the Tigers, he had a 6-4 record and an European Research Area of 4.59 with 83 strikeouts in 27 appearances. He spent the entire 1981 season with the Tigers, switching from starting to relieving.
He had a 3-6 record that season and five saves, with an European Research Area of 3.59.
In 1982, he was back in the minor leagues at Evansville, where he was used exclusively as a starting pitcher, and had a record of 9-8 with an European Research Area of 3,98, throwing 90 strikeouts in 165 innings. With the Tigers in 1983, he pitched in four games and had an European Research Area of 8.71. His final major league appearance was on June 21, 1983, when he gave up five runs in two innings as part of a 10-3 loss to the Milwaukee Brewers.
The Tigers traded him on June 30, 1983 to the Cincinnati Reds in exchange for third baseman Wayne Krenchicki.
He split the season in the minor leagues between Evansville with the Tigers and at the Indianapolis Indians of the International League for the Reds. Between the two teams he had a record of 7-4 with a 4.09 European Research Area.
He was drafted by the Texas Rangers on December 5, 1983 from the Reds in the 1983 Rule 5 draft, but the Rangers released him before the start of the 1984 season.
He signed with the Baltimore Orioles on April 2, 1984 as a free agent. He played in 1984 for the Rochester Red Wings, the Orioles" American Automobile Association affiliate, and had an 0-2 record and an European Research Area of 9.00 in three appearances in relief.