Jaggernauth had Nelon Pascal caught close to the wicket to bring the match to an end, and finish with match figures of nine for 105.
The result meant that T&T have now moved into third on 33, and Windwards have plunged to the bottom-of-the-table with 16 points.
T&T face second-placed Jamaica in the final round at Progress Park in Grenada, where the Championship will be decided.
A victory for T&T would give the title to Barbados and deny reigning champions Jamaica a third straight grab; a defeat for T&T would hand the Jamaicans the title ahead of the Barbadians; and a draw would also favour Barbados.
Jaggernauth used a mixture of off-spinners and googlies to bamboozle the bottom half of the Windwards’ batting.
Rawl Lewis still managed to hit the top score of 61. He struck five fours and three sixes from 77 balls in two hours, and Garey Mathurin made 31 in a seventh-wicket stand of 64.
T&T had early success, after the Windwards resumed from their overnight total of 129 for five, when Imran Khan trapped Shane Shillingford for one.
T&T then spent a little more than an hour battling Lewis and Mathurin with limited success before Jaggernauth made the breakthrough, Jaggernauth bowled Mathurin, and this opened the floodgates, as Windwards lost their last four wickets – including Lewis – for 17 runs in quick succession.
SCOREBOARD
TRINIDAD & TOBAGO 1st Innings 263
WINDWARD ISLANDS 1st Innings 188
TRINIDAD & TOBAGO 2nd Innings 297 for six declared
WINDWARD ISLANDS 2nd Innings (target: 373 runs)
(overnight 129 for five)
M. Bascombe c Bravo b Stewart 9
C. Emmanuel c wkpr G. Mohammed b Gabriel 10
+A. Fletcher c wkpr G. Mohammed b Khan 42
L. Sebastien lbw b Jaggernauth 26
*D.S. Smith c Bravo b S. Ganga 14
R. Lewis c Barath b Jaggernauth 61
S. Shillingford lbw b Khan 1
G. Mathurin b Jaggernauth 31
D. Butler c and b Jaggernauth 1
K. Peters not out 8
N. Pascal c S. Ganga b Jaggernauth 5
Extras (b5, lb2, nb2) 9
TOTAL (all out, 60.2 overs) 217
Fall of wickets: 1-9, 2-30, 3-89, 4-91, 5-129, 6-136, 7-200, 8-202, 9-211
Bowling: Gabriel 12-1-52-1 (nb2); Stewart 11-4-33-1; Jaggernauth 15.2-4-47-5; Khan 17-3-63-2; S. Ganga 5-1-15-1
Result: Trinidad & Tobago won by 155 runs
Points: Trinidad & Tobago 12, Windward Islands zero
Umpires: L. Kelly, D. Somwaru
Man-of-the-Match: Amit Jaggernauth (Trinidad & Tobago)
