Benjamin was born in Couva, Trinidad and Tobago, to parents Neil Sr. and Charlene.[1] In primary school, Neil discovered at an early age that he had a talent for his speed on the track. However, his focus would soon transition to football and credits his father and uncles, Glen and St. Nicholas, for his passion for the sport. At the age of 7, Benjamin enrolled in the youth program at TT Pro League club W Connection – based in his hometown of Couva.
Benjamin attended Naparima College in San Fernando, Trinidad and led the team to the Secondary Schools Football League (SSFL) South Zone title in 2010.[2] He later scored the lone goal in a 3–1 loss to St. Augustine Secondary, which witnessed Naps eliminated from the national Intercol Big Five competition.[3][4] In 2011, Benjamin was the joint-leading goal scorer with 10 goals in the under-17 reserve league while playing for W Connection and was named the most valuable player in the under-18 reserve league the following season.[5]
In September 2012, Benjamin traveled to Italy for a trial with Serie A club Genoa.[8] During his first week, he drew serious interest from Genoa after impressing the club with his speed and had his stay extended.[9] However, the trial proved unsuccessful and Neil was ultimately released to rejoin W Connection in November. Afterwards, Benjamin went on to enjoy an active second season with the Savonetta Boys after scoring four league goals and five in all competitions, including his first career hat-trick as a professional in a 4–0 win over eventual Pro League champions Defence Force on 6 May 2013.[10]
Neil opened the 2013–14 season as a regular substitute for W Connection playing primarily as a right-wing forward. During the 2013–14 CONCACAF Champions League, Benjamin made appearances in each of the Savonetta Boys' four group stage matches. On 8 August 2013, he came on for Mekeil Williams in the 62nd minute and later scored W Connection's lone goal of the competition in a 3–1 loss to Árabe Unido.[11] Two weeks later, Benjamin started in a scoreless draw at home against the Houston Dynamo of Major League Soccer. During the match, Neil had two late match-winning opportunities with one "horrific" open net miss and another shot hitting the crossbar.[12] Benjamin later had an impressive series of performances in the TOYOTA Classic and FA Trophy competitions.[13] On 18 December, he was named the most valuable player of the FA Trophy final after scoring the tying goal to send the match into a penalty shootout and lead the Savonetta Boys to the club's first FA Trophy crown in 11 years.[14] Afterwards, Benjamin experienced a dip in form with his lone league goal scored on 10 January 2014 in a narrow 2–1 win over Police.[15] He concluded his third season with W Connection with a string of substitute appearances to help lead the club to its fifth Pro League title and second in three years.[16]
He began his international career for the under-17 team during qualification for the 2011 CONCACAF U-17 Championship, where he made two starts in the midfield for the Soca Warriors against Cuba and Saint Kitts and Nevis.[19][20] He made a further second-half substitute appearance in the team's final group match against Bermuda to help Trinidad and Tobago top their qualification group.[21] In February 2011, during the continental competition, Benjamin started in consecutive matches against Jamaica and Guatemala.[22][23] However, in the quarterfinals, the Young Warriors were eliminated from the competition following a 2–0 defeat to Canada.[24]
^Shaun Fuentes (Trinidad and Tobago Football Federation) (19 August 2010). "U-17 men whip St Kitts in CFU opener". Soca Warriors Online. Retrieved 16 February 2014.
^Shaun Fuentes (Trinidad and Tobago Football Federation) (15 February 2011). "Henry scores two, T&T ties Jamaica 2–2". Soca Warriors Online. Retrieved 16 February 2014.