Milanovich's playing career lasted from 1996 to 2003 as a quarterback in the NFL for the Tampa Bay Buccaneers and Cleveland Browns, in NFL Europe for the Berlin Thunder, in the XFL for the Los Angeles Xtreme, in the Arena Football League for the Tampa Bay Storm, and in the CFL for the Calgary Stampeders.

Milanovich played as a true freshman, backing up John Kaleo and recording 1 touchdown and 1 interception across 11 games.

Prior to the 1995 season, Milanovich and four other Maryland players received suspensions for betting on college football and basketball games.

Milanovich struggled upon his return, throwing for two touchdowns and seven interceptions, though his senior season was the only one in which Maryland had a winning record.

Milanovich was named the MVP for the Blue squad in the Blue-Gray Classic, and completed 9 of 20 pass attempts for 175 yards and two touchdowns.

[3] After going undrafted in the 1996 NFL draft, Milanovich signed as a free agent with the Tampa Bay Buccaneers.

After being left unprotected by the Buccaneers in the 1999 NFL expansion draft, Milanovich was the only quarterback selected by the Cleveland Browns, but he never played for the team.

Milanovich was expected to be the starting quarterback for the XFL's Los Angeles Xtreme but lost the job to Tommy Maddox.

Between the 2004 and 2005 seasons, Milanovich was the quarterbacks coach and offensive coordinator for the now defunct Mansfield University Mountaineers football team.

[12] He named his coaching staff on January 21, 2020, but the 2020 CFL season was eventually cancelled due to the COVID-19 pandemic.

[17] After the team's offensive coordinator, Tommy Condell, was fired, Milanovich assumed play calling duties on August 7, 2023.

[20] He pleaded no contest and received a $550 fine, probation, 50 hours of community service and six-month driver's license suspension.