On the eve of WWE Money-in-the-Bank, the second NXT TakeOver: Chicago came to you, live on the WWE Network, from the Allstate Arena in Chicago. Three championships would be on the line in “The Windy City” as Aleister Black defends the NXT Championship against Lars Sullivan, Shayna Baszler defends the NXT Women’s Title against Nikki Cross, and The Undisputed Era’s Roderick Strong & Kyle O’Reilly defend the NXT Tag Team Titles against Danny Burch & Oney Lorcan. Plus, the intense and personal rivalry between Johnny Gargano and former friend and tag team partner Tommaso Ciampa would reach a new, extreme level as Gargano and Ciampa would wage war in a Chicago Street Fight. Also, the high-flying and innovative Ricochet would go one-on-one with the enigmatic Velveteen Dream.
- NXT Tag Team Championship: The Undisputed Era’s Roderick Strong & Kyle O’Reilly (c) (with Adam Cole) def. Danny Burch & Oney Lorcan by Roderick Strong (c) pinning Danny Burch following Total Elimination to retain.
- Ricochet def. Velveteen Dream by pin following the 630.
- NXT Women’s Championship: Shayna Baszler (c) def. Nikki Cross by submission to the Kirifuda Clutch to retain.
- NXT Championship: Aleister Black (c) def. Lars Sullivan by pin following Black Mass to retain.
- Chicago Street Fight: Tommaso Ciampa def. Johnny Gargano by pin following a DDT on the exposed ring mat.
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