As a senior, he received All-Central Ozark Conference honors at tackle on both offense and defense.

As a junior, teammate Max Jean-Gilles moved to offensive guard, allowing Roland to replace him as a starter at tackle.

As a senior, he contributed to the team defeating Louisiana State University by a score of 34–14, to win the 2005 SEC Championship Game.

On September 4, 2006, he signed as a free agent with the Tampa Bay Buccaneers and spent the season on the practice squad.

On October 2, he was promoted to the active roster and was declared inactive in 2 regular-season games (against the Indianapolis Colts and Tennessee Titans).

On December 21, he made his NFL debut against the Cleveland Browns, subbing in fourth quarter at right tackle for an injured Stacy Andrews.

His pass blocking helped the team rank ninth in league in fewest sacks allowed (29).

[12] Roland's father, Dennis Sr., served as the head football coach at Olivet Nazarene University from 1986 to 1990.