He joined the Hoosiers in 1978. He did not play in 1979, but became a regular through the 1980-1982 seasons. In 1982, he captained Indiana as it ran to the NCAA championship game. In that game, Indiana went up against Duke University and its top defenseman Joe Ulrich. Gregg scored the first goal, but Duke replied and the game ended tied at one all. The game was in its eighth overtime when Ulrich fouled Gregg just outside the box. He replied with a swerving free kick which found the net, giving Indiana its first national title. He would come in second in the balloting for the Hermann Trophy that year, losing to Ulrich.
Gregg was drafted be the Rowdies in 1982, as the number 1 draft choice in the NASL, out of NCAA Champion Indiana University, only days after the Hoosiers beat Duke 2-1. During the 1982 season with the Hoosiers, the fullback notched a total of 16 points (6 goals - 4 assists). 1982 honors included All-American status, selection to the 1982 Senior Bowl and the second consecutive National Sports Festival. The accomplished athlete also found time for studies, winning the IU varsity Club Academic Achievement Award (3.52 grade point average out of a possible 4.0 in finance) for the second consecutive years. Drafted as the first pick in December by both the MISL LA Lazers and the NASL Rowdies, Gregg decided on the Rowdies almost immediately and joined them in mid-January 1983. Gregg's arrival in Tampa was delayed by his January marriage to college sweetheart Nelle.
Appeared in 4 games during the 1982-83 Grand Prix Of Indoor Soccer, made his outdoor debut against the Tulsa Roughnecks on April 22nd at Tampa Stadium in a 4-3 win. He would appear in all 30 games. Winning him the NASL Rookie of the Year, Honorable Mention All-Star status and double team honors. The only player other than Rodney Marsh to be named both MVP and Most Popular Rowdie.
In 1984, Gregg was in fine form as he played in the first 10 games, before an injury caused him to miss the next 7. He returned on August 12th, against the San Diego Sockers in a 1-5 loss. Would continue at fullback for the rest of the last NASL season.
After the collapse of the NASL, the Rowdies traded him to the Minnesota Strikers of Major Indoor Soccer League. He remained with the Strikers through the 1987-1988 MISL season before retiring.
At the end of the 1983 NASL season, He joined the U.S. Olympic team as it prepared for the 1984 Summer Olympics in Los Angeles. Gregg played all three games for the U.S. at the Olympics, including scoring the U.S. goal in its 1-1 tie with Egypt. The U.S. finished the first round at 1-1-1 and failed to qualify for the second round.
Even before the Olympic games, he had earned his first cap with the U.S. national team in a May 20th, 1984 scoreless tie with Italy. He would go on to play a total of 12 times for the full national team between 1984 and 1985, including several qualification matches for the 1986 FIFA World Cup. His last national team game came in the May 31st, 1985 debacle in Torrance, California when the U.S. lost to Costa Rica. That loss in the last qualification game, cost the U.S. a spot in the finals.
Even before the Olympic games, he had earned his first cap with the U.S. national team in a May 20th, 1984 scoreless tie with Italy. He would go on to play a total of 12 times for the full national team between 1984 and 1985, including several qualification matches for the 1986 FIFA World Cup. His last national team game came in the May 31st, 1985 debacle in Torrance, California when the U.S. lost to Costa Rica. That loss in the last qualification game, cost the U.S. a spot in the finals.
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