Deering grew up in Plano, Texas, a suburb of Dallas, where he attended Plano Senior High School. He was twice selected as a Parade high school All-American and was the 1988 Texas high school player of the year his senior year. While in high school, he debuted with the U.S. U-16 national team for whom he played at the 1987 FIFA U-16 World Championship. During that tournament, Deering scored a goal in a 4–2 loss to South Korea. Deering was highly recruited out of high school and elected to play with Indiana University which had just won the NCAA Men's Soccer Championship. However, he left Indiana after only two seasons in order to pursue a professional career in Germany, having scored twelve goals and assisted on twelve others. He earned NCAAFirst-Team All-American honors his second, and final season, with Indiana. That year he was also the NCAA's post-season tournament's points leader with three goals and one assist.
Germany
Deering began his professional career with the SV Werder Bremen reserve team. After three years and no chance of playing for the Bremen first team, Deering moved to FC Schalke 04 in 1993 where he continued to languish playing for Schalke's amateur squad. In 1994, Deering played a single season with Rosenborg of the Norwegian Premier League. He returned to Germany the next year, becoming the first of several Americans to sign with Regionalliga team Kickers Emden. In 1996, he moved from Emden to German Second Division club VfL Wolfsburg and finally found a top German team which would play him. That season, he helped Wolfsburg gain promotion to the Bundesliga. The next year, Deering played fifteen games for Wolfsburg in its first year in the German top division.
MLS
In 1998, Deering expressed an interest in returning to the U.S. to play in Major League Soccer. He subsequently signed with the league, and on July 2, 1998, MLS allocated Deering to the Dallas Burn where he became a regular for the next seven years.
MISL
On January 24, 2004, Deering signed with the Dallas Sidekicks of Major Indoor Soccer League. The 2003–2004 season was nearly over and Deering played only nine games with the Sidekicks.
He earned his first cap when he came on for Hugo Perez in a December 18, 1993 loss to Germany. Deering would go on to play eighteen games for the U.S. national team, scoring his only national team goal in a March 14, 1998, 2–2 tie with Paraguay. When U.S. coach Steve Sampson sacked John Harkes, the team's primary defensive midfielder prior to the 1998 FIFA World Cup, Sampson moved Deering into that position. However, Deering played only a single game, a 0–2 loss to Germany, in the World Cup.
Post-playing career
Deering was the director of coaching for the Blackwatch Soccer Club in McKinney, Texas which merged with Solar Soccer Club in Dallas. He was the Director of coaching for Solar in McKinney and coached the Solar 98 and 96 Girls Gold teams. Currently he is the President and Director of Coaching for Dallas Rush FC in McKinney, TX. Deering now coaches club Dallas Rush.
