He signed as an undrafted free agent with the Arizona Cardinals on April 23, 2001. He made the team but played little in 2001, not getting a single rushing attempt. He did return 6 kickoffs. In 2002 Shipp would see many more opportunities. 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. In Week 11, he rushed for a season high 135 yards and a touchdown against the Oakland Raiders. He finished the year with a team leading 834 rushing yards on 188 carries and 9 total touchdowns. At the beginning of the 2003 season Shipp's status was somewhat unclear as the team had signed Emmitt Smith in the offseason. Despite Smith's presence Shipp again led the team in rushing with 830 yards on the season. His yards per carry went down to 3.6 however and he did not score a touchdown. He rushed for a career-high 165 yards against the San Francisco 49ers in a Week 7 win. In training camp in 2004, Shipp broke his leg and dislocated his ankle, forcing him to miss the entire 2004 season. He did not play at all that year. Following the missed 2004 season Shipp still remained with the Cardinals. In 2005, he was again the Cardinals' leading rusher, but this time with only 451 yards on 157 carries, for 2.9 yards per carry. In 2006 Shipp saw much less action, as the Cardinals had signed Edgerrin James. He rushed 17 times for 41 yards. He did have 4 touchdowns, scoring for the first time since 2002, including 3 touchdowns in one game on December 3 against the St. Louis Rams. In 2007, he had limited duty again, with 15 carries for 41 yards, still backing up James. In 2008, Shipp signed a 3-year contract with the Cardinals. However, he was released by the team on August 4.
Houston Texans
On August 18, 2008, Shipp agreed to terms with the Houston Texans, but was later released on August 29. His career NFL stats are 605 rushes for 2,197 yards and 11 rushing touchdowns. He has 109 receptions for 912 yards and 3 receiving touchdowns.
Shipp signed with the Las Vegas Locomotives of the United Football League on August 25, 2009. He finished the 2009 UFL season with 72 carries for 257 rushing yards, good for fourth in the league. Shipp's Locomotives defeated the Florida Tuskers 20-17 in overtime to win the inaugural UFL championship game. Shipp returned with the team for the 2010 season. The Locomotives won a second straight championship again defeating the Tuskers in the championship game. Shipp finished the regular season with 313 rushing yards on 117 carries and four rushing touchdowns. In the championship game he had 16 carries for 43 yards. In 2011 Shipp remained with the Locomotives for a third season, despite the UFL's continued financial problems. In only a four team league, the Locomotives went 3-1 with Shipp as their leading rusher. Shipp gained 164 yards on 49 carries and scored two touchdowns. The Locomotives did not win their third straight championship as they lost in the title game 17-3 to the Virginia Destroyers.
Coaching career
Since retiring from football Shipp has had various coaching stops over the past 4 seasons: 2012 he became the runningbacks coach of the Las Vegas Loco's of the UFL. 2013 he served as a coaching intern for the Arizona Cardinals 2014 he joined his alma matra UMass as the team's running backs coach 2015 he joined the New York Jets as the team's running backs coach. It was announced on January 3, 2017, that Shipp along with several other coaches were fired from the Jets' staff.