Cyprien received an athletic scholarship to attend Florida International University, where he played for the FIU Panthers football team from 2009 to 2012.

He finished second on the team with 78 tackles, recorded one interception, three breakups and forced two fumbles, and earned all-conference honorable mention selection.

[3] On January 26, 2013, Cyprien played in the Reese's Senior Bowl and recorded five combined tackles and was a part of Oakland Raiders' head coach Dennis Allen's North team that lost 21–16 to the South.

[5] During the draft process, Cyprien had private workouts and meetings with over 12 NFL teams, including the Cincinnati Bengals, Cleveland Browns, Jacksonville Jaguars, Washington Redskins, Atlanta Falcons, Carolina Panthers, Dallas Cowboys, Miami Dolphins, Arizona Cardinals, Tennessee Titans, San Francisco 49ers, and Houston Texans.

[17] Cyprien entered training camp slated as the starting strong safety after Dawan Landry departed for the New York Jets during free agency.

Although he suffered a hamstring injury, head coach Gus Bradley officially named him the starter to begin the regular season.

[19] On September 22, 2013, Cyprien recorded seven combined tackles and made his first career sack on Seattle Seahawks' quarterback Russell Wilson as the Jaguars lost 45–17.

[21] On December 1, 2013, Cyprien collected ten combined tackles, deflected a pass, and made the first interception of his career off of Cleveland Browns' quarterback Brandon Weeden in a 32–28 victory.

Cyprien finished his rookie season with 104 combined tackles (87 solo), six pass deflections, an interception, and a sack in 15 games and starts.

[28] Cyprien started the season-opener against the Carolina Panthers and recorded four combined tackles before leaving the 20–9 loss with a calf injury.

[31] On December 13, 2015, he made six combined tackles, intercepted a pass from Andrew Luck, and returned it for 48 yards during a 51–16 victory over the Indianapolis Colts.

In Week 12, Cyprien recorded six combined tackles and sacked Buffalo Bills' quarterback Tyrod Taylor during a 28–21 loss.

[38] The next week, Cyprien recorded a career-high 17 combined tackles as the Jaguars lost to the Houston Texans on the road by a score of 21–20.

[44] Cyprien started in the season-opener against the Oakland Raiders and recorded seven combined tackles before leaving the 26–16 loss with a hamstring injury that sidelined him for the next six games (Weeks 2–7).

[46] In Week 14, Cyprien made ten combined tackles and sacked Arizona Cardinals quarterback Blaine Gabbert in the 12–7 road loss.

[47] Cyprien finished his first season with the Titans with 57 combined tackles (38 solo), a sack, and a pass deflection in ten games and starts.

[50] The following week, he made seven combined tackles as the Titans lost in the AFC Divisional round to the New England Patriots by a score of 35–14.

He supplements his football earnings by investing in real estate, owning 13 properties in the Nashville, Jacksonville, and Miami areas as of 2018.