Off-spinner Amit Jaggernauth snatched four for 63 while leg-spinner Yannick Cariah finished with for 39, as the Leewards collapsed to 214 all out just before tea, in search of 335 for victory at Warner Park.
The 20-year-old Cariah, who also took three wickets in the first innings and struck 83 in T&T’s second innings, was voted Man-of-the-Match.
Resuming the day on 45 for two still 290 runs adrift of their target, the Leewards flourished early on through two successive half-century partnerships.
Orlando Peters and captain Sylvester Joseph, who saw the Leewards to the safety of the close on the third day, were positive in their approach as they extended their third wicket stand to 68.
Peters, not out on two overnight, stroked the top score of 45 from 163 balls in 200 minutes at the crease with four boundaries while the veteran Joseph struck two fours and a six in an innings spanning 101 balls and 115 minutes.
When leg-spinner Imran Khan bowled Joseph, wicketkeeper Devon Thomas paired with Peters to put on a further 52 for the fourth wicket.
Thomas, a right-hander, produced a brisk knock of 32 off 41 balls with three fours and a six before he fell on the stroke of lunch to a catch at mid-wicket off Cariah.
After the interval, wickets tumbled regularly despite 25 from Jahmar Hamilton and 20 from Tonito Willett, as the Leeward lost their last six wickets for 65 runs.
Jaggernauth ended the innings dramatically when he took three wickets in his 28th over to send the Leewards crashing from 214 for seven.
TRINIDAD & TOBAGO 279 all out (Adrian Barath 58, Yannick Ottley 58, Stephen Katwaroo 55, Ravi Rampaul 27; Quinton Boatswain 4-75, Gavin Tonge 2-52) and 249 (Yannick Cariah 83, Adrian Barath 71; Larry Joseph 4-66, Anthony Martin 3-60)
LEEWARD ISLANDS 194 (Sylvester Joseph 68, Austin Richards Jr 28, Montcin Hodge 24; Imran Khan 4-62, Yannick Cariah 3-35, Amit Jaggernauth 3-39) and 214 (Kenroy Peters 45, Sylvester Joseph 39, Devon Thomas 32, Jahmar Hamilton 25, Tonito Willett 20; Amit Jaggernauth 4-63, Yannic Cariah 3-39)
T&T 1st Innings 279
LEEWARDS 1st Innings 194
T&T 2nd Innings 249
LEEWARDS 2nd Innings (Target: 335 runs)
(overnight 45 for two)
A Richards Jr c wkp Katwaroo b Rampaul 16
M Hodge b Emrit 13
O Peters lbw b Cariah 45
*S Joseph b Imran Khan 39
+D Thomas c Jaggernauth b Cariah 32
J Hamilton c Jaggernauth b Cariah 25
T Willett b Jaggernauth 20
L Joseph c Imran Khan b Jaggernauth 8
G Tonge c Barath b Jaggernauth 5
A Martin not out 0
Q Boatswain c wkp Katwaroo b Jaggernauth 0
Extras (lb7, nb3, w1) 11
TOTAL (all out, 83.5 overs) 214
Fall of wickets: 1-25, 2-29, 3-97, 4-149, 5-169, 6-184, 7-201, 8-214, 9-214, 10-214.
Bowling: Emrit 9-4-24-1, Jaggernauth 27.5-7-63-4, Rampaul 9-1-22-1, Imran Khan 15-5-40-1, Cariah 17-5-39-3, Ottley 6-1-19-0.
Result: T&T won by 120 runs.
Points: T&T 12, Leewards 0.
Man-of-the-Match: Yannic Cariah.
Umpires: L Reifer Jr, N Malcolm.