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Terry Woodberry grew up in London, playing in the Chelsea FC youth system before moving to the United States to attend college at Southern Nazarene University. Woodberry first attended Southern Nazarene from 1981 to 1983 and then again from 1986 to 1987. He played two seasons of NAIA college soccer each during his two stints at the school. In 1986, he was an NAIA honorable mention All American and in 1987, he was a third team All American.
In 1987, Woodberry signed with the Oklahoma City Warriors of the Southwest Indoor Soccer League. He was the third leading scorer as the Warriors won the league championship. 1988, the Dallas Sidekicks of Major Indoor Soccer League drafted Woodberry in the fourth round (thirty-ninth overall). He spent three seasons in Dallas before moving to the San Diego Sockers for the 1991-1992 season. The Sockers won the MISL championship, the last in the league history. The league folded following the championship series and Woodberry moved to the Wichita Wings of the National Professional Soccer League (NPSL). For the 1993 outdoor season he was "loaned" to the Tulsa Roughnecks (USISL). He was a first team All Star in the 1993-1994 NPSL season. In 1994, he was with the Arizona Sandsharks of the Continental Indoor Soccer League where he earned first team All Star recognition. In 1996, the Sandsharks temporarily withdrew from the league and Woodberry rejoined the Sidekicks, now also playing in the CISL. That year, he was also selected by the Kansas City Wiz in the fourteenth round (136th overall) in the 1996 MLS Inaugural Player Draft. The Wiz waived him on March 26, 1996. Woodberry then began the 1995-1996 NPSL season with the Wichita Wings, but played only seven games before moving to the Detroit Rockers for the remainder of the season. In 1999, Woodberry returned to the Sidekicks which now played in the World Indoor Soccer League. In 2001, Woodberry and his teammates won the WISL championship.