He spent much of his childhood in Barbados, where his father Courtney Blackman served as Governor of the Central Bank and he attended the Harrison College School.

For two summers, Blackman's family lived on the Upper West Side in New York and he trained at the Port Washington Tennis Academy.

[2] Blackman beat future Grand Slam winners Michael Chang and Petr Korda en route to the semi-finals of the 1986 US Open Juniors and was also a semi-finalist at the same event a year later, with MaliVai Washington in the doubles.

[3] Blackman started on the Grand Prix tennis circuit in 1987 when, at the age of just 16, he appeared at Indianapolis and achieved a win over world number 74 Luiz Mattar.

[3] At Roland Garros he was unable to better his previous effort and again exited in the opening round, this time to countryman Bryan Shelton in four sets.