From 1995 to 2002 Darlington represented Guyana in 30 first-class matches, with his final appearance for the side coming against the Leeward Islands.
In 2010 he made his debut for the United States against the UAE in a pre-tournament warm up match for the 2010 ICC World Twenty20 Qualifier.
Later in February 2010, Darlington represented the United States in the 2010 ICC World Cricket League Division Five, where he ended the tournament as the leading wicket taker with 14 wickets as the United States gained promotion to the 2010 ICC World Cricket League Division Four in Italy.
[3] In 2020, Darlington was named head coach of the United States national under-19 cricket team.
[4] In 2023, Darlington was named interim head coach of the USA senior team for the 2023 ICC Cricket World Cup Qualifier Play-off in Namibia.