By the age of eight, Chanderpaul was playing for his village's cricket team, and would frequently bat for hours, being bowled at by various members of his family.

[9] He made his first-class cricket debut for Guyana at the age of 17, facing Leeward Islands in the 1991–92 Red Stripe Cup.

[12] He achieved his maiden first-class century in April 1993, playing for the West Indies Board President's XI against the touring Pakistanis.

[14] In 2007, he subsequently joined Durham as an overseas player, and helped the club collect its first major honour by top-scoring in their 2007 Friends Provident Trophy final win.

[22] Over the following couple of years, Chanderpaul was in and out of the West Indian Test side, missing a visit by Australia altogether.

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.

[29] Free of his foot injury, Chanderpaul enjoyed the best series of his career to that point when he scored centuries in three of the five Test matches against India.

[a][31] Later in that same series, the two sides scored exactly the same total in their respective first innings, and Australia then reached 417 in their second, leaving West Indies requiring 418 runs to win.

No side had ever successfully chased that many runs to win in a Test previously; writing for Cricinfo, Andrew Miller reported at the end of the third day that "Victory [for the West Indies] is as unlikely as ever, but it remains a remote possibility.

"[32] On the final two days, Ramnaresh Sarwan and Chanderpaul—batting with a broken finger—both reached centuries, and the West Indies completed the record run-chase with three wickets remaining.

[35] In late 2004, Digicel began a sponsorship deal with the West Indies cricket team, and caused division within the squad.

[37] In the first match of the series, Chanderpaul became only the second player, after Graham Dowling, to score a double century on his debut as captain in Test cricket.

[26] Only a resolute batting performance from Jacques Kallis rescues a draw for South Africa in the match, although Chanderpaul was criticised for both the timing of his declaration,[39] and later, negative field placings.

[40] For the second Test of the series, the West Indies were back to full-strength after the seven missing players cancelled their contracts with Cable & Wireless.

The former West Indian bowler, Colin Croft suggested that Chanderpaul "was filling a space until some else could take over the mantle.

In the Test match series against the Australians, Chanderpaul had amassed 442 runs in 6 innings, in 3 of which he had remained not out, at an average of 147.33, including two centuries and three half-centuries.

[5] Aged 41 at the announcement, Chanderpaul did not play for West Indies since May 2015,[60] and his subsequent exclusion was cited to be a result of poor performances in the home series against England, in which he averaged 15.33 in 3 matches.

[61] He was also dropped from the WICB contract in December 2015, signalling the selectors' intention to move forward with younger players, despite the fragility of the West Indies middle order.

He adopts this stance in order to see the ball clearly with both eyes, something he developed as a child when facing hostile fast bowling.

[62] Despite this, when he began playing Test cricket, he had a reasonably traditional stance, with his feet only angling slightly forwards.

[68] As his stance has developed throughout his time playing international cricket, his batting aggression has undergone a similar transformation.

He was first selected for the West Indies based on his attacking style of play; he cites Rohan Kanhai as one of his early influences.

"[29] The Australian spin bowler Shane Warne described Chanderpaul as "a bloke you needed to crowbar away from the crease,"[68] and he is often labelled as "limpet-like.

[74][75] In July 2022, Chanderpaul was appointed head coach of the United States women's national cricket team.