NXT Takeover: Chicago aired live on May 20th, 2017 on the WWE Network from the Allstate Arena in Chicago, IL.
- The show opens up with a video about underdogs in the city of Chicago. Bobby Roode tells the camera that the story of the underdog doesn't exist in his NXT.
- Roderick Strong def. Eric Young: Sanity comes out with Young, and Strong lays them out before the match so it's just him and Young to start off. Strong starts off strong and controls the pace against Young early on. Young mounts a brief comeback but Strong shuts him down with a series of forearm shots and a knee to the face. The action spills out to ringside and Killian drops Strong when the referee's back is turned. Back in the ring, Young takes control until he attempts a cross-body off the top and Strong blocks it with a dropkick. Strong hits some elbows and punches, then a series of clotheslines. Strong drops Young with a back breaker then hits a running knee in the corner. Strong hits a back suplex for a near-fall. They roll out to ringside where Young hits a neckbreaker on Young on the floor, and both men are down. Young hits a flying elbow off the top rope, then Sanity starts to get on the apron but Strong knocks them off. Strong and Young go to the top rope where Strong hits a knee to the face that sends Young flying down to ringside ontop of Sanity. Back in the ring, Young comes back with a boot to the face, but Strong comes back with another knee to the face. Strong hits his signature backbreaker for the win, then flees the ring as Sanity comes in after him.
- Pete Dunne def. Tyler Bate: Jim Ross comes out first to join the commentary team and gets a big pop from the Chicago crowd. Dunn controls the opening moments with mat wrestling and he works over Bate's left hand. Things spill out to ringside where Bates leaps off the ring steps with a flying elbow on Dunne. Dunne comes back with a vertical suplex onto the ring apron. Back in the ring, Dunne boots Bate in the face several times, then Bates comes back with a t-bone suplex. Bate throws Dunne in the corner where he hits a running European uppercut. Dunne comes back with a knee to the face and he attempts a suplex, but Bate gets out and hits a suplex of his own for a near-fall. Bate goes for a standing shooting star press but Dunne catches him in a triangle choke. Dunne hits some punches and elbows, but Bate picks him up and slams him with a powerbomb. Bate gets Dunne on his shoulders in the fireman's carry position and spins him around, then pins him for a two count. Dunne comes back with a forearm shot to the face and hits a powerbomb for a near-fall. The two men trade punches in the middle of the ring until Bate drops Dunne. Dunne comes back with a kick to the head and both men are down. They trade strikes again, then Bate attempts a tiger suplex but fails. Bate comes right back with a DDT that sends Dunne rolling out to ringside. Bate hits a moonsault off the top onto Dunne on the floor, then slides him in the ring for a corkscrew 450 splash off the top, but still only gets a two count. Dunne rolls outside and Bate attempts a suicide dive and misses. Dunne rolls him back in the ring and hits his finisher for the win to win the UK Championship.
- Asuka (c) def. Ruby Riot & Nikki Cross: Nikki gets taken out early on, then Ruby drops Asuka and sends her outside. Ruby gears up for a suicide dive but Nikki sideswipes her and drops her. All three women out to ringside now where Riot takes control. Ember Moon is shown watching in the crowd. Things go back in the ring where Asuka hits a missile dropkick off the top onto Nikki and she falls onto Ruby. Ruby hits some leg kicks on Asuka but Asuka stops her and hits a powerbomb. Asuka puts her in an ankle lock, but then Nikki runs in and hits Asuka from behind. Nikki and Ruby start going at it with strikes until Asuka comes back into the fray and hits Ruby. Ruby drops Asuka with a hurricanrana, then Ruby slams Nikki into the corner. Asuka takes Nikki outside and drops her with a knee to the face, then Ruby hits a suicide dive on Asuka outside. Ruby takes Nikki back in the ring for a senton drop off the top rope for a two count. Asuka hits a suplex on Ruby for another two count. Asuka grabs Nikki next, but Nikki fights away and hits a neckbreaker for a two count. Ruby superkicks Nikki which directly leads to Asuka hitting a German Suplex on Nikki. Ruby then kicks Asuka and attempts a senton drop off the top on her, but Asuka rolls out of the way and locks Ruby in the Asuka Lock. Nikki hits a splash on Asuka to break the Lock. Nikki takes Ruby out and sends her to the floor, then catches Asuka in the apron and unloads with strikes. Nikki drags Asuka over to a corner. Nikki with the hanging neckbreaker for a 2 count as Ruby breaks it up. Ruby and Nikki collide with crossbody attempts. Asuka tries to get back in it but she ends up on the floor as the other two go at it. Ruby drops Nikki with a Pele Kick but Asuka breaks up the pin with a running knee. Asuka stumbles over and falls on top of both opponents for the win.
- Bobby Roode (c) def. Hideo Itami: Itami attempst the Go 2 Sleep early on, but Roode escapes and rolls outside. Back in the ring, Itami hits a series of knee strikes to take control of the match. Itami works on Roode in the corner and attempts a Tornado DDT, but Roode fights him off and hits a Blockbuster for a two count. Roode controls the next few moments of the match and starts slapping Itami on the back of the head while he's down. Itami gets back up and slaps Roode across the face, then hits a flurry of strikes that leaves Roode down. Itami drops Roode's neck across the top rope, then hits a flying clothesline off the top turnbuckle for a two count. Itami tees off on Roode with kicks until Roode ducks one and attempts a rollup. Itami grabs Roode's arm to block the pin and attempts an arm submission but it doesn't happen. Itami throws more kicks at Roode then goes for a running knee but Roode catches him with a spinebuster for a two count. Roode attempts a DDT, but Itami fights out. Itami goes for the Go 2 Sleep, but Roode gets out and drops Itami's throat over the top rope. Roode and Itami brawl around ringside before rolling back inside where they exchange forearm strikes. Itami drops Roode in the corner and hits a running dropkick on him. Roode escapes a Go 2 Sleep attempt by Itami and hits the implant DDT for a two count. Roode is selling a shoulder injury, and Itami is selling a leg injury. Itami hits a Go 2 Sleep out of nowhere on Roode, but Roode immediately rolls outside and Itami is unable to follow up with the pin. Itami gets Roode back in the ring and slaps him in the face several times. Itami goes for another Go 2 Sleep, but Roode gets out and hits not one but two Glorious DDTs for the win to retain the NXT Title.
- Kevin Owens, Pat Patterson and others are shown in the crowd watching the show at the Allstate Arena.
- Authors of Pain (c) def. DIY: All four men start brawling right off the bell, with DIY getting the upper hand and sending the Authors outside. Ciampa hits a drop two hold on Akam into the ring steps, then hits a cross body on him. Gargano hits a suicide dive on Rezar, then DIY grabs the ladder. Back in the ring, Akam side suplexes Gargano ontop of Ciampa. The Authors start climbing a ladder towards the belts hanging above the ring, but Ciampa grabs another ladders and uses it to bat them off. DIY clams the ladder onto the Authors then start climbing, but the Authors push them off. The Authors take some time to beat down Ciampa and Gargano to keep them grounded before they go back for the belts. They start to climb the ladder, but decide against it in favor of beating down DIY some more. The Authors hit Ciampa and Gargano with a ladder and send them rolling outside. The Authors grab another big ladder and slide it in the ring, then they take two other tables and prop them up between the ring and fan barricade like tables. The Authors go to powerbomb DIY into the propped up ladders, but Ciampa and Gargano both escape. DIY comes back with strikes on the Authors, then they lay them ontop of the propped up tables. Ciampa and Gargano both climb up a big ladder standing upright and they both hit splashes onto Rezar and Akam through the ladders below. Back in the ring, all four men start climbing ladders towards the belts until DIY pushes the Authors off. Paul Ellering runs in and pushes over the ladder, so Gargano superkicks him. The Authors come back in and lay out both Ciampa and Gargno. The Authors deliver a ladder shot right to the face of Gargano then they start climbing towards the Titles. Ciampa runs up the ladder and suplexes Rezar off of it through another ladder in the corner of the ring. Akam starts going for the Title but Gargano grabs his leg to stop him. Ciampa and Gargano both superkick Rezar a couple times, then they go for the Titles. The Authors come back in and shove the ladder over, then deliver a couple of powerbombs to the DIY members. Rezar and Akam immediately climb up and grab the Tag Titles while Gargano and Ciampa are recovering from the powerbombs.
- After the match, the copyright logo shows and DIY heads up the ramp. Out of nowhere, Ciampa turns on Gargano and throws him into the Titantron. Ciampa hits two running knees to the face, and Gargano tries to hug Ciampa's leg. Ciampa takes Gargano to the top of the announce table, then slams him through some production equipment on the floor. Referees check on Gargano and Ciampa watches as Takeover goes off the air.