| Mermaid Winner |
Survivor Leland |
Bolan, Watkins, Crimmins, Hartman, Frank, Klein, Strietmann |
| 12 & Under |
Leland Yacht Club Rocks |
Irwin, Irwin, Kiernan, Ansley , Sutton, Zimmerman |
| Teen |
Bar-Birthday-Cruise |
Petty, Roberts, Martin, Hearne, Carlson, Byerle |
| Family |
Splish Splash Fishtown's Takin a Bath |
Coleman, Kiernan, Riley |
| 50 & Over |
Her Last Commodore Cruise |
Wellborn, Keeble, Frazier |
| Cooks Choice |
Happy 60th Mermaid |
Owsley, Zimmerman, Sutton, Byerle, Machiels, Wellborn, Crimmins, Shatto, Frasier |
| Style Award 2019 |
Miss Leland |
Hijazi, Sagges, Brossey, Boesel, Voss, Nield |
| Most Nostalgic |
Happy Birthday Mr. Barbecruise |
Winn Scherer, Quinn Irwin, Carter Sutton, Walker Sutton |
| Cutest Angels |
Leland Angels |
Revel and Hearne |
| The Judges Award |
Judging the Judges |
Will Sawyer, Hayden Murray, Willa Murray, Jackson Mello |
