Frye was drafted by the Texas Rangers in the 30th round of the 1988 amateur draft and made his big league debut with them on July 9, 1992, at Arlington Stadium during a 14–4 Rangers victory over the Cleveland Indians. Frye went 2-for-3, including a triple, walk, RBI and three runs, as the starting second baseman and leadoff hitter. His first career home run came on July 24, 1992, off Baltimore Orioles pitcher Arthur Rhodes at Oriole Park at Camden Yards. He missed the 1993 season due to injury.
In 1996, after hitting just .238 in 49 games with the Rangers' American Association affiliate Oklahoma City 89ers, Frye was released. That same day, June 5, he was signed as a free agent with the Boston Red Sox. He had a career year in 1997 when he hit .310 with 6 home runs in 127 games. He missed the entire 1998 season due to an injured left knee[1] but returned for the 1999 season, playing in 47 games.
On December 11, 2000, Frye signed as a free agent with the Toronto Blue Jays.[citation needed] On August 17, 2001, he became the second Blue Jay in history to hit for the cycle. The first Blue Jays player to hit for the cycle was Kelly Gruber, who happened to be in attendance that day.[2]
Frye's final big league appearance came on September 20, 2001, as he pinch-hit for catcher Darrin Fletcher in the 8th inning of a 12–6 loss to the Orioles. Frye flew out to left field and remained in the game at second base, replacing Homer Bush defensively.