The Happy Gilmore star was awarded worst actor and actress for his portrayal of the brother and sister of the title.
Sandler might feel comforted that even Godfather star Al Pacino wasn’t spared, as he received an award for worst supporting actor.
Other awards that Sandler racked up on the night were for worst screenplay as co-writer of the movie, and worst ensemble for his performance alongside co-stars Pacino and Katie Holmes.
Razzies founder John Wilson joked: “He didn’t play triplets, but he couldn’t have won more awards if he had.
“Adam Sandler has a pretty much basic attitude of: ‘No matter how dumb I make it, my fans are going to pay to see it.’
“I guess it’s more about the complete lack of any genuine effort or concern or pride.
“An attitude of this is good enough, but when you consider what they’re charging for movie tickets today, it wasn’t good enough.”
The comedy actor might feel unfairly picked on by the awards ceremony, as his accolade for worst actor was shared with Just Go With It, which he appeared in alongside Friends star Jennifer Aniston last year.
The Razzies, officially titled the Golden Raspberries, were founded by film buff Wilson in 1980 to celebrate the worst films released that year, but this is the first time a single film has swept all of the awards.
The spoof ceremony took place on Sunday night at a magic shop in Santa Monica, California. Nominees were picked by 657 voters across the US and in 17 other countries.
Despite the historic nature of the event, Sandler joined a long list of nominees, including Halle Berry, Kevin Costner and Sandra Bullock, who haven’t turned up to claim their prizes.