Set 86 runs from 60 overs for victory, the Windward Islands reached their target losing three wickets with Stewart unbeaten on 53.
The Windward Islands took the first innings advantage after bowling Barbados out for 121 and then responding with 146 for eight.
Resuming on 47 for three, with Daniel Chesham on 29, Barbados only added 63 runs to its total.
Chesham (33) and Nagee Holder (22) were the main contributors as Alick Athanaze (3 for 21) and Narun Singh (3 for 46) restricted the scoring.
The Windwards had an early scare with the loss of two wickets for 13 runs. But opener Johann Jeremiah, who was joined by Stewart, took the score to 62 before he was caught behind by wicketkeeper Michael Stewart for 23. The Windwards’ captain took control of the situation and steered his side to victory over Barbados. His unbeaten innings of 53 included five fours from 49 balls.
Summarised scores: Barbados 121 all out off 31.2 overs (Limar Pierce 45, Joshua Bishop 23, Alick Athanaze 4 for 31, Shane Roberts 2 for 20) & 110 all out off 59.2 overs (Daniel Chesham 33, Nagee Holder 22, Athanaze 3 for 21, Narun Singh 3 for 46); Windwards 146 for 8 off 40.4 overs (Nick Elibox 49, Johnell Eugene 44, Kemar Burrowes 5 for 39) & 86 for 3 off 26.4 overs (Emmanuel Stewart 53 not out, Johann Jeremian 23, Nagee Holder 1 for 4).
