AAW Windy City Classic XV was a professional wrestling event produced by AAW: Professional Wrestling Redefined It took place on December 28, 2019 at the 115 Bourbon Street in Merrionette Park, Illinois. It was broadcast on FITE TV.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Myron Reed defeated Ace Austin, Air Wolf, Clayton Gainz, Colt Cabana and Josh Briggs
- Kimber Lee defeated Hyan
- Killer Kross defeated Matthew Justice
- The Masked Good Brother #3 defeats Jimmy Jacobs in a Dog Collar Match
- Kris Statlander defeated Jessicka Havok (c) to win the AAW Women's Championship
- Curt Stallion & Jake Something defeated David Starr & Eddie Kingston in a Tag Team Bourbon Street Fight Match
- Hakim Zane defeated PACO (c) to win a AAW Heritage Championship
- The Besties In The World (Davey Vega & Mat Fitchett) (c) defeated oVe (Jake Crist & Sami Callihan) to retain the AAW Tag Team Championship
- Mance Warner defeated Josh Alexander (c) to win the AAW Heavyweight Championship
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