In March 1996 and 1997 Oliver and his fellow players lead his team, the Mason City Mohawks, to two state tournament wins. Head coach at the time was Robert Horner, father of player and future Hawkeye, Jeff Horner. Oliver was not drafted in the 2001 NBA draft but played two seasons with the Golden State Warriors, who waived Oliver on December 5, 2002. With the Warriors, Oliver played a mostly backup role in 35 games, averaging 1.8 points, 0.7 rebounds, and 1.3 assists per game.[3]
Oliver's final NBA game was played on December 3, 2002, in a 110–89 win over the Denver Nuggets where he recorded 5 points and 1 rebound.
On February 3, 2003, he signed with the Greenville Groove of the NBA Development League (D-League). The Groove waived Oliver on February 23, and Oliver signed with the D-League team Asheville Altitude two days later.[4] In October 2003, Oliver signed with the expansion team of the USBL, Cedar Rapids River Raiders, in his home state of Iowa; the River Raiders would begin play in the spring of 2004.[5] He then signed with the Dakota Wizards of the CBA in February 2004.[6] The Wizards won the 2004 CBA title, and Oliver was a backup for the Wizards.[7]
In 2011, he became the head of basketball operations at North Dakota.[11] In 2014, he became an assistant basketball coach at Illinois State.[12] On April 20, 2017, Oliver was named an assistant at Wisconsin under coach Greg Gard.[13]