On 2 October 2001 Daren Sammy made his List A debut at the age of 17. Playing in the Red Stripe Bowl for the Northern Windward Islands against Jamaica he bowled nine overs without taking a wicket and scored 25 runs before he was run out as his team slid to defeat. Playing three matches Sammy was his team's second-highest run-scorer with 90 runs, and took one wicket. Sammy was a member of the West Indies team to the 2002 Under-19 World Cup, which was held that year in New Zealand; he made 22 runs and took three wickets. Other members of that team, which lost to Australia in the semi-final, included Dwayne Bravo, Narsingh Deonarine, Ravi Rampaul, Shane Shillingford, Lendl Simmons, and Gavin Tonge all of whom went on to play for the West Indies senior team.

Upon his return from New Zealand, Sammy was picked to attend the Shell Cricket Academy at St. George's University in Grenada in 2002. The scheme aimed to help what were considered the Caribbean's "brightest cricketing prospects" develop skills to help them professionally, including areas such as money management to complement their cricketing ability. Other notable players in that class – just a handful would go on to play senior cricket for West Indies – included Dwayne Smith, Narsingh Deonarine, Carlton Baugh, Daren Powell, and Omari Banks.

On 31 January 2003, Sammy made his first-class debut for the Windward Islands against Barbados in the 2002/03 Carib Beer Cup. Batting at number seven, he scored no runs before being dismissed by spin bowler Sulieman Benn in the first innings, but fared better in the secon