Breeland attended Allendale-Fairfax High School in Allendale, South Carolina, where he played football and basketball and ran track. In football, he played quarterback and defensive back. He was an All-state selection by The State and All-Atlantic Region team member by PrepStar. As a junior, he had 95 rushes for 789 yards with 12 touchdowns on offense, and totalled 76 tackles on defense. He led the Tigers to a 10-2 record as a senior after rushing for 1,270 yards and 15 touchdowns. He was also a starter on the basketball team.
In track & field, Breeland won the state title in the 400m hurdles as a sophomore and junior, and helped his team reach the state title in track as a junior. He captured two state titles at the 2010 SCHSL State Championships, winning the 110m hurdles (15.06s) and the 400m hurdles (54.78s). He earned a tenth-place finish in the 300m hurdles at the 2010 Bob Hayes Invitational at 40.69 seconds. He was also timed at 4.41 in the 40-yard dash and posted a 280-pound bench press and 450-pound squat.
Regarded as a three-star recruit by Rivals.com, Breeland was regarded as the No. 22 safety in the nation and No. 6 player in South Carolina by Scout.com, and the No. 56 safety in the nation by ESPN.com. He chose Clemson over Penn State, South Carolina, Tennessee, and Virginia Tech.
On May 16, 2014, he signed a four-year, $2.64 million contract with the Redskins. He became a starter following a season-ending injury to DeAngelo Hall early in the season. In the Week 7 win against the Tennessee Titans, he recorded his first career interception on quarterback Charlie Whitehurst. He had a breakout performance in the Week 8 win against the Dallas Cowboys. He covered starting wide receiver Dez Bryant, limiting him to only three receptions, forced DeMarco Murray to fumble which was recovered by safety Brandon Meriweather, and broke up a pass on fourth down sealing the Redskins' overtime victory. In the Week 16 game against the Philadelphia Eagles, he intercepted quarterback Mark Sanchez late in the fourth quarter to help seal the Redskins victory.
On July 31, 2015, the second day of training camp, it was announced that Breeland would be suspended for the first game of the 2015 season for the citation he was given by Virginia Commonwealth University police for possession of marijuana on August 11, 2014. On exactly the same day, he was injured during camp practice and was carted off the field. It was later announced that he sprained his MCL with a recovery period of four to six weeks and would not participate for the rest of training camp. In Week 5, he recorded the his first interception of the season against Atlanta Falcons quarterback Matt Ryan. In Week 6, Breeland had a solid performance against the New York Jets, having recorded one interception, one forced fumble, and two fumble recoveries.