After graduating from Homewood-Flossmoor High, Dillard played two years of college basketball for Southern Illinois University. After the 2009–10 season, Dillard transferred to Dayton.[2] He had to sit out one season under NCAA rules.[3] He was named to the All-Atlantic 10 Second Team, as a junior[4] and senior.
Dillard failed to be drafted at the 2013 NBA draft. On August 7, 2013, he signed with A.S. Junior Casale of Italy, for the 2013–14 season.[6]
On July 4, 2014, he signed with VEF Rīga of Latvia.[7] On November 8, 2014, he parted ways with VEF Rīga.[8] On December 8, 2014, he signed with Élan Béarnais Pau-Orthez of France, for the rest of the season.[9]
On August 1, 2015, he signed with MHP Riesen Ludwigsburg of Germany, for the 2015–16 season.[10] However, on September 4, 2015, he parted ways with Ludwigsburg, before appearing in a game for them.[11]
On October 27, 2015, he signed with Cholet Basket of France.[12] On November 25, 2015, he left Cholet, and signed with the Greek club Apollon Patras.[13]
On April 2, 2016, he signed with the Belgian club Antwerp Giants, for the rest of the season.[14]
On July 27, 2016, Dillard signed with Turkish club Pınar Karşıyaka.[15] On December 4, 2016, he was excused from the team, with poor playing performance being cited as the reasons for the decision.[16][17] In the wake of the falling out with his club, he did not re-join the team at all during the rest of December, while instead looking for another gig elsewhere.[18]
