But just when it looked the pair would both reach the close unbeaten, wicket-keeper Ramdin was caught by a diving Paul Collingwood at third slip off Durham team-mate Liam Plunkett for 60.
West Indies, at stumps on the third day, were 363 for seven and still 190 behind England's 553 for five declared.
Chanderpaul, who three years ago against England at Lord's scored 128 not out and 97 not out in a Test the West Indies lost by 210 runs, was showing similar resilience now with 63 not out.
He received excellent support from wicket-keeper Ramdin in a seventh-wicket stand of 83 in 25 overs.
Left-arm spinner Monty Panesar took four for 108 in 31 overs, including a 29-over spell broken only by lunch and tea.
But he went wicketless in the final session.
Chanderpaul, together with Dwayne Bravo, who made a rapid 56, put on 92 in 20 overs for the sixth wicket.
West Indies resumed after tea on 217 for five, 336 behind, after Panesar had taken four for 52 in 17 overs.
Their hopes of avoiding the follow-on had already been bolstered by Matthew Hoggard, one of four specialist bowlers, leaving the field with a thigh strain.
Chanderpaul, a left-hander, began the session 26 not out with Bravo on 14.
All-rounder Bravo drove Panesar, 25, through mid-wicket to go to 46 and completed a run-a-ball 50 when he lofted him for the first six of the match.
But Bravo gave his innings away when pulling Paul Collingwood to Alastair Cook at square leg, the medium-pacer taking only his second Test wicket.
West Indies were now 279 for six.
Chanderpaul went to a patient 123-ball fifty with his sixth four, a fortunate edge off Collingwood to third man.
Meanwhile Ramdin showed his batting ability by cover-driving and cutting fast bowler Stephen Harmison for four.
England took the new ball in the 84th over with West Indies 314 for six.
Ramdin then completed his fifth Test fifty with his tenth four, a resounding cover-drive off Durham quick Harmison as he reached the landmark in 62 balls.
Harmison, increasingly wayward, failed to take advantage of the new ball in a spell of four overs for 29.
Ramdin's single off Collingwood then saw West Indies avoid the follow-on as they reached 354.
Panesar, who'd dismissed Devon Smith with his first ball of the morning session, took a further three wickets for 13 runs in 36 balls.
He had West Indies captain Ramnaresh Sarwan, hiding his bat behind his pad, given out lbw for 35 by Pakistan umpire Asad Rauf.
Panesar, again showing how he could provide both variety and control in an otherwise all seam attack, ended Daren Ganga's near three-hour innings when the opener, on 49 was lbw.
Runako Morton, who scored a century in the tourists' lone warm-up match against Somerset, also fell lbw to Panesar's arm-ball after he too didn't offer a shot.
Plunkett had bowled Chris Gayle for 30 with a delivery that swung in and clipped the left-hander's off-stump after he'd played down the wrong line.
Strauss, confident England had enough runs on the board, declared before play began Saturday in the opening match of a four-Test series.
That meant Matt Prior, the first England wicket-keeper to score a century on his Test debut, finished on 126 not out off just 128 balls with 19 boundaries.
Ian Bell was 109 not out having shared an unbroken stand of 190 with Prior, who subsequently kept tidily.
Cook (105) and Collingwood (111) also reached three figures.
This was the first time four England batsmen had scored centuries in the same Test innings since 1938.