An overpowering right-handed pitcher, Shikles played in the Boston Red Sox farm system from 1986 to 1992. He pitched for the Greensboro Hornets in 1986, the Winter Haven Red Sox in 1987, and the New Britain Red Sox in 1988. He was with the Triple A Pawtucket Red Sox from 1989 to 1992. In 1993, he pitched for the Triple A Tacoma Tigers in the farm system of the Oakland Athletics. In the early 1980s, he pitched for Jefferson City High School and the Jefferson City Cougars. He also played for East Central College in Union, Missouri. In 1984 and 1985, Shikles was an All-Conference pitcher for Western Kentucky University, setting single season records for victories, strikeouts, and scoreless innings. In 1982, he pitched for the West County Browns team that finished fifth at the NBC tournament in Wichita, Kansas. He also played for the Browns in 1983. In 1984, he pitched for the Springfield Rifles in the Central Illinois Collegiate League. Shikles spent the 1985 season with the Grand Rapids Sullivans, an independent team in Grand Rapids, Michigan. In 1994, he pitched in the Mon-Clair League for the Waterloo Buds under coach Vern Moehrs. From 2010 to 2013, Shikles played in the Bud Light Senior Men’s League on the East Side. Shikles coached youth baseball teams for over 10 years.