The first official senior limited overs game in the West Indies was played on 18 March 1970, between a touring Duke of Norfolk's XI and the Barbados team.

[8][9][10] The next season, the tournament was renamed the Geddes Grant/Harrison Line Trophy, named after two large shipping companies in the area, with Leeward Islands and Jamaica progressing from the two groups.

However, the final, scheduled to be held at the Antigua Recreation Ground on 8 April 1977, was rained off, and the teams shared the trophy.

Telemaque stuck in, however, adding 39 with Ian Allen, before number 11 Dominique Lewis came in to bat in his List A debut with 17 needed.

The next season saw two new teams for the first time, as Bermuda and Canada joined, but both finished bottom of their groups with neither managing to win any of their six games.

By the end of the 1990s, the Red Stripe Bowl had been established as an early-season feature, where the semi-finals and finals being held in Jamaica and Busta Cup games commencing after tournament's completion.

Jamaica won the 20th century's last regional one day tournament after prevailing over the Leeward Islands in the final.

[11] 2000–01 saw two more teams invited, with the United States beating Barbados by two wickets, a result that didn't prevent the Americans coming last in the group.

The Guyanese team had been offered the light earlier, but not realising they were ahead on Duckworth-Lewis, they chose to bat on, and it was enough to win the game.

[14] In December 2013, NAGICO Insurance was announced as the new title sponsor of the Regional Super50 with the winning team taking home the Clive Lloyd Trophy – named in honour of the former West Indies captain.

[16] In February 2019 Bermuda based Colonial Group International was announced as the new title sponsors of the regional one day competition now dubbed the CG Insurance Super 50.