His high school coach Bob Milloy noted: "What you're going to get from him is he's a lockdown corner, started both ways for me, and if you don't keep an eye on him, he'll run a punt or kickoff back.

"[5] During the 2010 recruiting season, Countess was pursued by many top collegiate football programs including Notre Dame, Stanford, Penn State, Michigan, Tennessee, Arkansas, Wisconsin, West Virginia, Pitt, Georgia Tech, Purdue, Maryland, Cincinnati, Louisville, Duke, Illinois, Virginia, and Wake Forest.

[13] ESPN.com called him "a natural cover guy with good size and speed," and noted that he has "all the tools to be an outstanding player in college.

"[13] Three weeks after Countess committed to Michigan, the school's head coach Rich Rodriguez was fired.

After graduating, he would decide to transfer to Auburn University to play out his final year of NCAA eligibility as a redshirt senior.

Countess saw his first substantial playing time for the 2011 Michigan Wolverines football team in the fourth quarter of a 28–7 victory over San Diego State on September 24, 2011.

[14] In less than one quarter, Countess accumulated seven tackles and broke up a pass in the endzone from quarterback Ryan Lindley.

"[15][16] The following week, Countess again drew praise for forcing a fumble and leading the team in tackles in a 58–0 win over Minnesota.

[18][19][20][21] Countess injured his anterior cruciate ligament in the season opener for the 2012 Michigan Wolverines football team against Alabama.

[25] After a brief recruiting process with various different schools, on May 26 he announced he would be a graduate transfer for the 2015 Auburn Tigers football team,[26] and his enrollment was official by May 28.

Countess was elevated to the active roster and won Super Bowl LVI when the Rams defeated the Cincinnati Bengals.

[48][49] On January 26, 2023, Countess signed with the New Jersey Generals of the United States Football League (USFL).