| Junior Carnival Mas 1999 |
| Port of Spain Junior Carnival 1999 |
| PoS - Junior Band Winner - Non-Schools 1999 |
| PoS - Junior Band Winner - Non-Schools Large Bands |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Carnival Time Again | Rosalind Gabriel |
| PoS - Junior Band Winner - Non-Schools Medium Bands |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Carnival Time Again | Rosalind Gabriel |
| PoS - Junior Band Winner - Non-Schools Small Bands |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Let's Make Music | Elizabeth Spence's |
| PoS - Junior Band Winner - Schools 1999 |
| PoS - Junior Band Winner - Schools Large Bands |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Take a Look Through My Kaleidoscope | St Joseph Girls and Boys |
| PoS - Junior Band Winner - Schools Medium Bands |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Headlines From the Pages of the Express | Success Laventille Composite School |
| PoS - Junior Band Winner - Schools Small Bands |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Beauty of Bush MedicineBarbara Punch and Amoco Galeota |
| PoS - Junior King 1999 | <
| Position | Portrayal | Individual (Band)/Band |
| 1 | Chief Pontiac | Kareem Edmund |
| PoS - Junior Queen 1999 | <
| Position | Portrayal | Individual (Band)/Band |
| 1 | Spirit of Fire | Alexandra Bailey |
| PoS - Male Individual of the Year 1999 | <
| Position | Portrayal | Individual (Band)/Band |
| 1 | The Ring Master | Darren Murray |
| PoS - Female Individual of the Yearn 1999 | <
| Position | Portrayal | Individual (Band)/Band |
| 1 | Spirit of Fire | Alexandra Bailey |
| Senior Carnival Mas 1999 |
| Port of Spain Carnival 1999 |
| PoS - Band of the Year |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Dynasty | Legends {Big Mike Antoino & Ian McKenzie) |
| 2 | Trapeze | Wayne Berkeley |
| 3 | Lost Tribe | Peter Minshall |
| PoS - Large Band of the Year |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Dynasty | Legends {Big Mike Antoino & Ian McKenzie) |
| 2 | Lost Tribe | Peter Minshall |
| 3 | Jewels of the Nile | Barbarossa |
| PoS - Medium Band of the Year |
| Position | Portrayal | Individual (Band)/Band |
| 1 | The Jewelled Box | The Rampage Committee |
| 2 | Savage Garden | Trini Revellers |
| 3 | Muthos | Stephen Derek |
| PoS - Small Band of the Year |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Conceptions of Africa | Churchill George |
| 2 | Pontiac | Henry Ramdin and Associates |
| 3 | Dance Caribbean | Robert Miller |
| PoS - Mini Bband |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Nicest Africa | Four Roads Love Vibes |
| PoS - Uptown Band of the Year |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Trapeze | Wayne Berkeley |
| PoS - Queen of the Day on Monday |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Anra Bobb | Hera, Queen of Heaven |
| PoS - King of J'Ouvert |
| Position | Portrayal | Individual (Band)/Band |
| 1 | Caroni To Jump Start 1999 Crop | Phillip Montano |
| PoS - Queen of J'Ouvert |
| Position | Portrayal | Individual (Band)/Band |
| 1 | The Winner of the 1998 Miss Universe, Wendy Fitzwilliam | Gloria Jones |
| Jouvert Realm |
| Position | Portrayal | Individual (Band)/Band |
| 1 | | Diable |
| Limbo Competition 1999 |
| Position | Individual (Group) |
| 1 | Nydia Byron |
| Flag Waving Competition 1999 |
| Position | Individual (Steelband) |
| 1 | >Heather Henderson-Gordon (Phase II Pan Groove) |
| Senior Calypso ~ Soca ~ Chutney-Soca Monarchs 1999 |
| Calypso Monarch 1999 |
| Position | Calypsonian(s)/Band | Tune #1 & Tune #2 |
| 1 | Singing Sandra | Voices from the Ghetto & Song for Healing |
| 2 | Sugar Aloes | This Stage is Mine & Power of Prayers |
| 3 | Gypsy | Soul of a Nation & Last of the Better Days |
| Road March 1999 |
| Position | Calypsonian(s)/Band | Tune |
| 1 | Sanell Dempster - Blue Ventures | The River |
| 2 | Kurt Allen | Dus Dem |
| 3 | Atlantik | Who to Blame |
| Soca Monarch 1999 |
| Position | Calypsonian(s)/Band | Tune #1 & Tune #2 |
| 1 | Kurt Allen | Dus Dem |
| 2 | Iwer George | Iwer & 1/2 |
| 3 | Superblue | Countdown |
| Soca Chutney Monarch 1999 |
| Position | Calypsonian(s)/Band | Tune #1 & Tune #2 |
| 1 | Rikki Jai | Rosie Balena & Galeekay Morah Godinaa |
| Calypso Queen 1999 |
| Position | Calypsonian(s)/Band | Tune #1 & Tune #2 |
| 1 | Shirlaine Hindrickson | Spirit of All Women & Amandla My People |
| Young Kings Monarch 1999 |
| Position | Calypsonian(s)/Band | Tune #1 & Tune #2 |
| 1 | Wayne Rodriguez | Pull Down the Fence & I Remember Africa |
| Pan Kaiso Monarch 1999 |
| Position | Calypsonian(s)/Band | Tune #1 & Tune #2 |
| 1 | Original De Fosto Himself | |
| Ragga Soca Monarch 1999 |
| Position | Calypsonian(s)/Band | Tune |
| 1 | Iwer George | Iwer and a Half |
| Gospelypso 1999 |
| Position | Calypsonian(s)/Band | Tune |
| 1 | Sean Daniel | One A Day |
| Tobago National Calypso Monarch 1999 |
| Position | Calypsonian(s)/Band | #1 & Tune #2 |
| 1 | Henson Wright aka. Prince | Stand up and Fight for your Family & Fantasy Island |
| Tobago Extempo Winner 1999 |
| Position | Calypsonian(s)/Band |
| 1 | Joseph 'Tempo' Caesar |
| Best Musical Instrumental Bands |
| Position | Calypsonian(s)/Band |
| 1 | Charlie's Roots |
| 2 | Square One |
| 3 | Roy Cape & Kaiso Allstars |
| Extempo, Humorous, Social Commentary & Political Commentary 1999 |
| Extempo |
| Position | Calypsonian(s)/Band | Tune |
| 1 | Black Sage | I Beat You Once, I Could Beat You Again |
| Humorous |
| Position | Calypsonian(s)/Band | Tune |
| 1 | Bomber | Cases |
| Social Commentary |
| Position | Calypsonian(s)/Band | Tune |
| 1 | Singing Sandra | Voices from the Ghetto |
| Political Commentary |
| Position | Calypsonian(s)/Band | Tune |
| 1 | Sugar Aloes | This Stage Is Mine |
