Shivnarine Chanderpaul was born in Unity Village, Guyana. His father, Khemraj Chanderpaul, helped to nurture his cricketing ability as a youngster. By the age of eight, Chanderpaul was playing for his village's cricket team, and was frequently bat for hours, being bowled at by various members of his family. His father initially took him to the Everest club in Georgetown, but there was not a place for him at the club, and so he instead joined the Demerara Cricket Club. He appeared for the club's under-16 side while only ten. He was later given an opportunity at the Georgetown Cricket Club.
He made his first-class cricket debut for Guyana at the age of 17, facing Leeward Islands in the 1991–92 Red Stripe Cup. He was run out for a duck in his first innings, but scored 90 runs in the second. His List A debut followed a few days later, against Barbados, in which Chanderpaul did not get a chance to bat in a match with no result. He achieved his maiden first-class century in April 1993, playing for the West Indies Board President's XI against the touring Pakistanis. After taking four wickets in the Pakistanis' innings, Chanderpaul was one of three West Indians to score a century, scoring 140 runs, and remaining not out.
During the English summer of 1993, Chanderpaul travelled with the West Indies Under-19 cricket team to England. He was the team's most successful batsman during the Test series, scoring 372 runs at an batting average of 124.00, including a score of 203 not out in the first Test, at Trent Bridge in Nottingham. In the 1993–94 Red Stripe Cup, Chanderpaul was near the top of the batting averages, and, according to the Wisden Cricketers' Almanack, he was a "contentious selection" for the subsequent Test series against England, in which he was picked as an all-rounder who could bowl leg breaks as well as bat. He bowled 16 overs in England's first innings without taking a wicket, and scored 62 runs in the West Indies reply. Chanderpaul played four Tests during his debut series, and was third amongst West Indian batsmen in terms of both runs scored and batting average, getting 288 runs at 57.60.
Over the following couple of years, Chanderpaul was in and out of the West Indian Test side, missing a visit by Australia altogether. During this time, he achieved the highest first-class score of his career, in a 1995–96 Red Stripe Cup match against Jamaica. In the first-innings of the match, which was eventually drawn, he scored 303 not out from 478 deliveries. In his first 18 Test matches, Chanderpaul scored 1,232 runs at an average of 49.28, but despite scoring thirteen half-centuries, his highest score was 82; a Test century eluded him. He reached the milestone in his nineteenth Test, scoring 137 against India. Just over a month later, he repeated the feat in One Day International cricket, striking his maiden century in the format, scoring 109 runs, also against India.
Chanderpaul scored a further century in each of 1998, in a Test match against England, and 1999, in an ODI against South Africa. In the latter match, Chanderpaul and Carl Hooper were the only West Indian batsmen to reach double figures while batting – Chanderpaul scored 150, and Hopper reached 108. Their partnership of 226 remains a record in ODIs for the West Indies, and Chanderpaul's individual total is his highest in ODIs. During this early period of his international career, Chanderpaul suffered with a negative reputation. Along with his failure to convert half-centuries into centuries, he had a tendency to miss matches which was perceived as hypochondria. He was also in the news for late-night partying; on one occasion in 1999, he shot a policeman in the mistaken belief that he was a thief. His career took a turn for the positive in 2000, when he had surgery on his foot to remove a floating bone.