Shipp played high school football at the Passaic County Technical Institute in Wayne, New Jersey.
[4] Shipp attended the University of Massachusetts Amherst and was a letterman for the UMass Minutemen football team.
He capped the season by rushing for 244 yards and three scores in the team's improbable 55–43 victory over the top-ranked Georgia Southern Eagles in the 1998 NCAA Division I-AA Football Championship Game.
[citation needed] He signed as an undrafted free agent with the Arizona Cardinals on April 23, 2001.
He had his breakout game in a Week 4 win against the New York Giants when he rushed for 92 yards on 17 carries and scored two touchdowns.
At the beginning of the 2003 season Shipp's status was somewhat unclear as the team had signed Emmitt Smith in the offseason.
In training camp in 2004, Shipp broke his leg and dislocated his ankle, forcing him to miss the entire 2004 season and he was placed on injured reserve.
Shipp signed with the Las Vegas Locomotives of the United Football League on August 25, 2009.
Shipp's Locomotives defeated the Florida Tuskers 20–17 in overtime to win the inaugural UFL championship game.
The Locomotives did not win their third straight championship as they lost in the title game 17–3 to the Virginia Destroyers.