Milacki played college baseball for Yavapai Community College, where future teammate Curt Schilling later pitched. The San Diego Padres drafted Milacki in the first round of the January phase of the 1983 Major League Baseball (MLB) draft, but he did not sign. The Baltimore Orioles drafted him in the second round of the June 1983 draft.[1][2] Milacki made his MLB debut with the Orioles in 1988, starting three games as a September call-up. He conceded only 2 runs and 9 hits in 25 innings. In his rookie season of 1989, Milacki led the American League with 36 games started, posting a 14–12 record with a career-best 3.74 ERA. He set a franchise record by pitching 243 innings as a rookie. Perhaps due to that workload, he was limited by shoulder tendonitis the following year.[1]
On April 23, 1989, Milacki pitched a rare complete gameshutout against the Minnesota Twins in which he faced the minimum 27 batters; he allowed 3 hits and 2 walks.[3]
On July 13, 1991, the Orioles defeated the Oakland A's 2–0 on a combined no-hitter. Milacki pitched the first six innings of the game, with no runs on no hits, three walks and three strikeouts.[4] He was pulled from the game after a line drive struck him on the arm, despite the batter being retired when the ball bounced towards first base. Mike Flanagan, Mark Williamson, and Gregg Olson each followed up with a no-hit scoreless inning to complete the no-hitter.[5]