Joseph Bagdonavich, the label's CEO, announced recently on entertainment programs ER and E Prime a $3-million winner-takes-all lyrical clash at Sting, which is celebrating its 30-year anniversary.
Ninja Man, also a contender, will have the duffle bag of cash live on stage to hand over to the winner.
The much-touted event, set for Jamworld Entertainment Complex, Portmore, St Catherine on December 26, will feature international artiste 2 Chainz, dancehall legend Super Cat and current icons including Beenie Man and Mavado.
Bagdonavich, via his company, officially became a full-time partner of Sting, with founder Isaiah Laing last year, after a few years behind the scenes.
The event is dubbed as 'The greatest one-night show on Earth'.
To celebrate this momentous occasion, which has never happened in the event's 30-year history, DSR has released a commemorative single, Downsound Christmas, which features label artistes Ninja Man, Ishawna, Harry Toddler, Don Husky and Naazir.
The track was produced by Bagdonavich and Scatta Burrell and will be marketed by DSR's marketing arm, Contractor Music.
"The song is already generating interests," said marketing director Sean 'Contractor' Edwards.
The label has enjoyed a number of successful collaborations, namely Ishawna and Specialist's Do For Love and Dweet, featuring Ninja Man and Specialist.
Ninja Man was recently victorious in a sound clash against popular radio disc jock GT Taylor at the Irie FM street dance. Ishawna was also engaged in a sound clash at Famous Nightclub for the STAR's All-Star Face Off.
Naazir and Don Husky continue to work hard in studio and are set to release new tracks.
The entire Downsound Records clique, which includes reggae sensation Nature, will perform at Sting.