Finwood was a standout shortstop at VMI, where he was named to the SoCon's All-North Division team three times. His.399 batting average remains sixth in school history. He also ranks highly on the program's all-time lists for hits and runs. He began coaching at VMI, serving as an assistant from 1989 through 1991 before being elevated to head coach. In his three years as a head coach, the Keydets went from 2 wins in 1991 to 21 wins in both 1993 and 1994, and played in the 1993 Southern Conference Baseball Tournamentchampionship game.
Finwood then moved to VCU, serving as assistant for four years and associate head coach for two. The Rams won more than 40 games in both 1998 and 1999, including a school record 46 in 1998. Both seasons, VCU earned trips to the NCAA Division I Baseball Championship and won CAA regular season titles in 1997 and 1998. He then moved to Auburn where he worked as an assistant for five seasons. He was responsible for the Tiger defense and also served as recruiting coordinator. Auburn recorded the two highest fielding percentages in school history, and ranked highly in both the SEC and nationally. The Tigers reached four NCAA Tournaments.
After his time at Auburn, Finwood earned the head coaching position at WKU. From his first to his third season, the Hilltoppers improved by 11 conference wins, claimed a conference tournament title, and reached the first of two straight NCAA Regionals. In 2009, WKU won 42 games, a share of the regular season title, and earned an at-large bid to the NCAA Tournament. Finwood saw 17 Hilltoppers drafted, 55 sign professional contracts, and three players reached Major League Baseball. WKU ranked highly in defense, finishing third in the nation in 2009, and fifteenth in 2011.
In June 2011, Finwood accepted the head coaching position at Old Dominion. The Monarchs improved from last to fourth in the CAA in the course of his first two seasons. However, due to the fact that ODU was moving to Conference USA the CAA officials ruled that they were ineligible for the conference tournament after winning 30 games and what would have been the third seed in the conference tournament. In 2014 Coach Finwood gave ODU its first ever C-USA victory in a 2–1 extra inning win on the road over then 15th ranked Rice Owls for his 300th career win. In just his third season at Old Dominion Coach Finwood lead the Monarchs to their first ever win over the number 1 ranked team in the country with an 8–1 victory over the Virginia Cavaliers at Harbor Park in Norfolk, reached the semifinals of the 2014 Conference USA Baseball Tournament, and earned an at-large bid in the Columbia, SC Regional of the 2014 NCAA Tournament, the school's eight appearance and first since 2000. The 2014 team finished the year third in the NCAA in double plays turned and first in Conference USA in double plays, doubles, HBPs, runs, stolen bases, and second in triples. In his four years at Old Dominion to date Finwood has had five players drafted in the MLB Draft, two All-Americans, and several All-Conference selections as well as two victories over a #1 ranked team.
