1999–2000 Red Stripe Bowl
| Dates | 27 October – 7 November 1999 |
|---|---|
| Administrator(s) | WICB |
| Cricket format | List A (50 overs) |
| Tournament format(s) | Group stage, finals |
| Champions | Jamaica (6th title) |
| Participants | 8 |
| Matches | 15 |
| Most runs | Sylvester Joseph (244) |
| Most wickets | Neil McGarrell (9) |
The 1999–2000 Red Stripe Bowl was the 26th season of what is now the Regional Super50, the domestic limited-overs cricket competition for the countries of the West Indies Cricket Board (WICB). It ran from 27 October to 7 November 1999.
Eight teams contested the competition – the six regular teams of West Indian domestic cricket (Barbados, Guyana, Jamaica, the Leeward Islands, Trinidad and Tobago, and the Windward Islands), plus two invited international teams from the ICC Americas region (Bermuda and Canada). The tournament was impacted by rain, with three matches (including the final) being interrupted and another three (including a semi-final) being abandoned entirely. Jamaica eventually defeated the Leeward Islands in the final to win their sixth domestic one-day title. Leeward Islands batsman Sylvester Joseph led the tournament in runs, while Guyana's Neil McGarrell took the most wickets.