The Challenge of the Immortals matches were the Arcane Horde (represented by team captain UltraMantis Black and the Batiri [Obariyon (Chris Estrada) and Kodama (Louie Rodriguez)], the other member was Oleg the Usurper (Josh Thorman)) vs. Crown and Court (represented by Jervis Cottonbelly and Los Ice Creams [Ice Cream Jr. and El Hijo del Ice Cream, the other member was team captain Princess Kimberlee (Kimberly Frankele)), the Wrecking Crew (represented by the Devastation Corporation [team captain Max Smashmaster (Sebastian Reese) and Flex Rumblecrunch (Sean Burke)] and Jaka (Jonny Mangue), the other member was the Corporation's Blaster McMassive (Thomas Stintsman)) vs. the Nightmare Warriors (represented by Frightmare (Stephen Delicato), Blind Rage (Timothy P. Vassa) and Silver Ant, the other member was team captain Hallowicked (Robert Goodwin)), the Snake Pit (represented by Eddie Kingston (Edward Moore), the other members were team captain Ophidian, Shynron (Shyn Ron) and Argus) vs. the Gentleman's Club (represented by Drew Gulak, the other members were team captain Chuck Taylor (Dustin Howard), Orange Cassidy and the Swamp Monster), Dasher's Dugout (represented by the Throwbacks [team captain Dasher Hatfield and "Mr. Touchdown" Mark Angelosetti] and Icarus (Ronald Grams), the other member was Heidi Lovelace (Dori Elizabeth Prange)) vs. Battle Hive (represented by team captain Amasis (Desean Pratt), Worker Ant (Nelson Ortiz) and "Smooth Sailin'" Ashley Remington (Brett Giehl), the other member was Fire Ant), and the Snake Pit (represented by team captain Ophidian and Shynron, the other members were Eddie Kingston and Argus) vs. Die Bruderschaft des Kreuzes (represented by team captain Jakob Hammermeier and Soldier Ant, the other members were Pinkie Sanchez (Adam Ortega) and Nokken).
The match between the Arcane Horde and Crown and Court was UltraMantis Black's last match until Chikara Tabula Rasa (2017). He retired due to leg injuries in September 2015 but was able to come back for the "lost" Season 17. In the pre-match promo, Mantis, Obariyon and Kodama talked about the problems their team had been having in the tournament and Mantis asked them what they wanted. They whispered something to him and Mantis said, "It's a deal." After Mantis' retirement, he would bring back the Batiri's teammate Kobald.
There was supposed to have been a match between "Juke Joint" Lucas Calhoun and Missile Assault Ant (R.B. Banks). Instead, Kevin Condron and Calhoun tried to recruit Missile to join them, with Condron telling Missile that joining with them will enable him to fly like the condor he is. The word "condor" angered Missile, due to how his team the Colony: Xtreme Force (Missile Assault Ant, Orbit Adventure Ant and Arctic Rescue Ant) were mercenaries put together by CHIKARA's former corrupt Director of Fun Wink Vavasseur, whose corporation the Titor Conglomerate used the paramilitary force Condor Security, who were the ones that had shut down CHIKARA on June 2, 2013 at Chikara Aniversario: Never Compromise (2013).
The Heidi Lovelace-Argus match was Heidi's first successful CHIKARA Young Lions Cup defense. She only defended the Cup twice, due in part to the Challenge of the Immortals tournament and in part to her commitments with other promotions. She would ultimately hold the Cup for 427 days, the second longest reign ever behind Hallowicked, who was the inaugural Champion and held it for 603 days.
The Hallowicked-Oleg the Usurper match was Hallowicked's second successful CHIKARA Grand Championship defense.