Milstead attended Lackey High School, where he was a two-time All-State offensive lineman and helped lead his team to a Class B state championship in 1986. He participated in the Big 33 Football Classic game between the Maryland and Pennsylvania All-stars. He also practiced track. He accepted a football scholarship from Delaware State University, where he became a four-year starter at left guard. As a junior, he helped Delaware State average 298.7 rushing yards per game and 5.2 yards per rush. Finishing the season as the NCAA Division I-AA No. 2 ranked rushing offense, including a school record 518-yard rushing performance against Towson State University. As a senior, he helped his team register 380 yards rushing against Northeastern University. He never missed a game or a practice, while making 42 straight starts at left guard. He was selected first-team All-MEAC three straight years and also received Division I-AAAll-American honors in 1991. In 2003, he was inducted into the Delaware State Athletic Hall of Fame.
Milstead was selected by the Dallas Cowboys in the fifth round of the 1992 NFL Draft. On August 25, he was traded to the Cleveland Browns in exchange for a conditional draft choice.
Cleveland Browns
On September 3, 1992, he was placed on the injured reserve list with a nerve problem in his back. He was released by the Cleveland Browns on September 1, 1993. He was later re-signed and spent 11 games on the inactive list. He was waived on August 28, 1994.
San Francisco 49ers
Milstead was signed by the San Francisco 49ers on September 15, 1994. The next year, he started a career-high 12 games. He was released at the end of training camp on August 25, 1997 and later re-signed in October, that season he went on to appear in 4 games and was inactive in 5.
Washington Redskins
On March 3, 1998, he was signed as a free agent by the Washington Redskins and went on to start 11 games. In 1999, he was inactive for the first 5 games, before being released on October 23. He was re-signed on November 9, 1999, after Keith Sims was injured.
In 2000, he signed with the Denver Broncos and was released on August 17.
Personal life
Milstead coached the Lackey High School football team to 2 state appearances at Ravens stadium. He coached the offensive line at Delaware State University. In 2016, he took over as the head football coach at La Plata High School in La Plata, Maryland. Milstead was named head football coach at Delaware State on January 30, 2018.
