England face a quest for survival after West Indies made 749 for nine declared thanks to a masterful 261-run partnership between double centurion Ramnaresh Sarwan and Denesh Ramdin.
The tourists, who survived two overs at the end of the fourth day of the fourth Test to close on six without loss, trail by 143 runs and now have virtually no chance of winning the series which West Indies lead 1-0 with one match remaining.
Sarwan fell just nine runs short of a triple century, after batting from the evening of the second day, while wicketkeeper Ramdin made 166 before being bowled by five-wicket Graeme Swann.
The West Indies score, the ninth highest innings total in a test match, sets up an unexpectedly tricky final day for Andrew Strauss's side after they made 600 for six declared in their first innings.
No team has ever lost a Test match after making such a big first innings total but West Indies will take heart from the first Test when they bowled a panicking England out for 51.
That, however, was on a very different wicket than the placid surface at the Kensington Oval and a draw still remains the most likely outcome. That would leave England needing to win in next week's Test in Trinidad to tie the series.
STYLISH SARWAN
Once again the elegant and poised Sarwan, who has scored three centuries in four innings in this series and made 94 the only time he fell short, was the dominating figure as he picked up from his 184 on Saturday.
The Guyanese right-hander picked up the second double century of career early in the morning session and along with Ramdin played with confidence and concentration to take West Indies to 483 for five by lunch.
The runs then flowed easily for both batsmen as England struggled to pose a threat and Sarwan seemed set for his first triple century before being bowled by a rare quality, late-swinging delivery from Ryan Sidebottom.
If England thought that the end of Sarwan's textbook innings, which lasted 699 minutes and 452 balls, would lead to a swift dismissal of the tail they were sorely mistaken.
West Indies were just five runs shot of England's total when Jerome Taylor, once a tailender but now a lively number eight, came out to join Ramdin and he proceeded to make hay.
Taylor took West Indies past England's total by dismissively hooking Sidebottom into the Greenidge and Haynes stand for six and went on to hit 53 in 62 balls including two more sixes.
Ramdin, who had batted with impressive shot selection and guile, then stepped up the tempo, adding a further 77 runs in partnerships with Sulieman Benn and Daren Powell.
West Indies declared after Ramdin finally went, giving off-spinner Swann his second five wicket performance of the series -- just reward for his inventive bowling, the pick of England's otherwise unthreatening attack.
Fidel Edwards and Daren Powell had just an over each at Strauss and Alastair Cook, enough to act as a reminder that West Indies have something England have sorely lacked in their two days of toil -- real, aggressive pace bowling.
With Jerome Taylor, who ripped through them in Jamaica, rested and with the new ball England will need to be on their guard.
Scorecard
England (1st innings): 600-6 declared (A. Strauss 142, A. Cook 94, P. Collingwood 96, R. Bopara 104, T. Ambrose 76 not out
West Indies (1st innings): (overnight 398-5)
D. Smith lbw b Swann 55
C. Gayle lbw b Anderson 6
R. Sarwan b Sidebottom 291
R. Hinds lbw b Swann 15
S. Chanderpaul lbw b Anderson 70
B. Nash lbw b Swann 33
D. Ramdin b Swann 166
J. Taylor b Swann 53
S. Benn c Ambrose b Anderson 14
D. Powell not out 13
Extras: (b-15 lb-11 w-1 nb-6) 33
Total: (nine wickets declared,194.4 overs) 749
Fall of wickets: 1-13, 2-121, 3-159, 4-281, 5-334, 6-595, 7-672, 8-701, 9-749.
Bowling: Anderson 37-9-125-3; Sidebottom 35-4-146-1; Broad 32-4-113-0 (1w); Swann 50.4-8-165-5; Pietersen 9-1-38-0; Bopara 13-0-66-0 (4nb); Collingwood 16-1-51-0; Shah 2-0-19-0 (2nb)
England (2nd innings):
A. Strauss not out 5
A. Cook not out 0
Extras: (nb-1) 1
Total: (for no wicket, 2 overs) 6
To bat: O. Shah, K. Pietersen, P. Collingwood, R. Bopara, T. Ambrose, S. Broad, J. Anderson, G. Swann, R. Sidebottom
Bowling: Edwards 1-0-2-0, Powell 1-0-4-0.