Ramdin formerly captained the West Indies, Guyana Amazon Warriors, Trinidad and Tobago and the Combined Campuses and Colleges.

According to Ramdin he did not receive much coaching early in his career, though he did have sessions with David Williams and Jeff Dujon in which he worked on his wicket-keeping.

When the West Indies toured Sri Lanka in July and August 2005, the 19-year-old Ramdin was the only wicket-keeper in the 15-man squad, taking over from the incumbent Courtney Browne.

[13] The West Indies did not register a century partnership until the fourth innings of the series when Ramdin, who scored 71, combined with Dwayne Bravo in just his seventh Test.

However, Ramdin went on to cement his place as the West Indies wicket keeper in all forms of the game and was the vice-captain at one point, following the resignation from that position of Ramnaresh Sarwan.

[21] The run of poor form meant Ramdin's central contract with the West Indies Cricket Board (WICB) was not renewed in August 2010.

[22] After a 2010–11 season in which Ramdin scored 460 runs in the Regional Four Day Competition,[21] he was recalled to the team for the ODI series against India.

[26] When the West Indies toured India in November and December Ramdin was the first-choice wicket-keeper for the ODI leg and played in all five matches.

[23] After recovering from the injury Ramdin was recalled to the Test squad to tour England in May and July, replacing Baugh who had not contributed as many runs as the selectors hoped.

When I look back, today perhaps with age, I have become wiser and would not have taken that piece of paper out of my trouser's pocket,"..."I have put the past behind and now myself and Viv are good friends.

Ramdin has hit only one half-century since his recall to the West Indies one-day side in October 2011 and has been dropped in several recent matches both during the Champions Trophy and the home tri-series which also featured India and Sri Lanka.

In Ramdin's absence West Indies used opener Johnson Charles behind the stumps, and haven't picked any specialist wicketkeeper in the squad.

Ramdin's knock was also his third century in an away test, equalling Clyde Walcott's record for most overseas hundreds by a West Indies wicketkeeper.

Ramdin scored 128, the first century by a West Indies wicket-keeper in ODIs though the regional side eventually fell short by 25 runs, to concede the series 2–1.

He then and there notched the highest ODI score by a West Indian batsman at home in the Caribbean surpassing Desmond Haynes' 152 not out against India at Bourda in Georgetown, Guyana in 1989.

[45] On 3 June 2018, he was selected to play for the Montreal Tigers in the players' draft for the inaugural edition of the Global T20 Canada tournament.