[1] He played on the state championship team as a junior and was a contributing factor to their success in the following season; finishing with eight receiving touchdowns as a senior.

During the 2008 Muck Bowl against rival Pahokee High School, Benjamin was covered by Janoris Jenkins and was able to make a touchdown reception.

He tied Stanford's Chris Owusu and Georgia Tech's Stephen Hill for the best 40-yard dash time among all wide receivers at the combine.

66 team representatives and scouts from the NFL and CFL attended, including Pittsburgh Steelers' head coach Mike Tomlin.

[18] Head coach Pat Shurmur named him the fourth wide receiver behind Mohamed Massaquoi, Greg Little, and Josh Gordon.

[19] He made his professional regular season debut in the Cleveland Browns' season-opener against the Philadelphia Eagles and had one reception for 12-yards and a carry for 35-yards during their 17–16 loss.

[21] On September 23, 2012, Benjamin caught two passes for 44-yards and scored his first career touchdown in the Browns' 24–14 loss to the Buffalo Bills.

[27] Unfortunately, head coach Pat Shurmur was fired after the Cleveland Browns finished last in the AFC North with a 4–12 record.

[28] He entered an open competition for the vacant starting wide receiver role after the departure of Mohamed Massaquoi.

[29] Head coach Rob Chudzinski named Benjamin the starting punt and kick returner after Josh Cribbs departed in free agency.

[34] Head coach Mike Pettine was hired by the Browns for the 2014 season and held an open competition for the starting wide receiver role after Josh Gordon was suspended in August.

Benjamin competed with newly acquired free agents Nate Burleson, Miles Austin, and Andrew Hawkins.

[35] Benjamin played in the Cleveland Browns' season-opener at the Pittsburgh Steelers and caught two passes for 20-yards and a touchdown during the 30–27 loss.

[37] During a Week 15 matchup against the Cincinnati Bengals, Benjamin had two punt returns for 24-yards and made his first career tackle on Bengal's linebacker Rey Maualuga after he intercepted a pass attempt by quarterback Johnny Manziel, intended for receiver Taylor Gabriel, and returned it 33-yards during the Browns 30–0 loss.

Head coach Mike Pettine surprisingly named Benjamin the starting wide receiver for the first time of his career, along with Andrew Hawkins, after he had a productive training camp where he was called the "most improved teammate" by Donte Whitner.

Head coach Mike McCoy named him and Allen the official starters to begin the regular season.

[53] He made his official San Diego Chargers' debut in their season-opener at the Kansas City Chiefs and caught seven passes for 32-yards in a 33–27 loss.

[54] The next week, Benjamin made six catches for 115 receiving yards and caught his first touchdown as a member of the Chargers on a 45-yard pass from Philip Rivers in their 38–14 win against the Jacksonville Jaguars.

[58] It was reported that Benjamin dealt with multiple injuries throughout the season that limited his playing time and ability to start all 16 games.

[59] In the Los Angeles Chargers' season-opener against the Denver Broncos on Monday Night Football, Benjamin recorded three receptions for 43-yards and caught a 38-yard receiving touchdown from quarterback Philip Rivers in their 24–21 loss.

[60] On September 24, 2017, Benjamin caught five passes for a season-high 105 receiving yards in Los Angeles' 24–10 loss to the Kansas City Chiefs.