The Fun Bet Between Buffalo Rapper And Jacksonville Comedian

When you consider the fact that, when Sunday, January 11, 2026, comes around, the Buffalo Bills and Jacksonville Jaguars will have only played each other a total of 21 times since the Jaguars entered the NFL, it's pretty interesting that the rivalry between these two teams has grown so much.

Including two playoff games, the Bills and Jaguars Jacksonville and Buffalo are tied with both 10 victories each, and the 2025/26 Wild Card matchup between these two teams will decide who takes the lead in this new rivalry. While the two teams are tied in their overall win/lose records, the Jaguars have beaten the Bills when it truly counts: in the playoffs.

On the two times these teams have faced each other in the postseason, on December 28, 1996, and January 7, 2018, Jacksonville has sent the Bills home for the season.

Buffalo Rapper Conway The Machine Challenges Jacksonville Comedian Lil Duval To A Big Football Bet>

Now that these teams are facing each other in the playoffs again, the wagers are picking up all over the country, and it's not just in the sports books.

Earlier in the day on Friday, January 9, 2026, we learned about a big bet that the Mayors of Buffalo and Jacksonville made on the outcome of the game, and now two of the biggest entertainers who call these two cities home are jumping in on the betting action.

Buffalo-born rapper Conway The Machine took to the internets to make a friendly and fun bet with Jacksonville-born Rapper and Comedian Lil Duval:

If Buffalo wins, Lil Duval will come up to Buffalo and do a show in Western New York, with all the proceeds going to Conway's charity: Conway Cares.
If Jacksonville wins, then Conway will head to Northeast Florida to perform a show wherever Duval wants and will also send him 100 wings from Wingnutz.

This is all love, competition, and respect... It’s about football, culture, and giving back. Bills Mafia knows what time it is.
-Conway The Machine

The Buffalo love runs big all through the 716, so people all over Western New York are looking forward to a big Bills win and a show featuring Lil Duval.