| card/ date | match | match type | title(s) |
|---|
 CHIKARA Every Man For Himself
Dec 22nd 2016 | Dasher Hatfield | def. | Ashley Vox, Bullet Ant, Cajun Crawdad, Delmi Exo, Donald Kluger, El Hijo del Ice Cream, Hallowicked, Heidi Lovelace, Hermit Crab, Icarus, Ice Cream Jr., Jasper Tippins, Jeremy Leary, Juan Francisco de Coronado, Kobald, Lucas Calhoun, Mark Angelosetti, Missile Assault Man, Nytehawk, Officer Warren Barksdale, Oleg the Usurper, Ophidian, Razerhawk, Rick Roland, Rock Lobster, Sloan Caprice, Solo Darling, The Proletariat Boar of Moldova, Travis Huckabee, Ultramantis Black, Wani, Worker Ant II | Infinite Gauntlet | |
CHIKARA Supremacy
Dec 3rd 2016 | Dasher Hatfield & Estonian ThunderFrog & Fire Ant & Heidi Lovelace & Missile Assault Man & Oleg the Usurper & Ophidian & Princess Kimberlee | def. | Frightmare & Hallowicked & Icarus & Jigsaw & Kobald & Kodama & Mark Angelosetti & Obariyon | Torneo Cibernetico | |
CHIKARA Hour of Power 4
Nov 13th 2016 | Kobald & Mark Angelosetti & Obariyon | def. (pin) | Fire Ant & Oleg the Usurper & Ophidian | 6-person tag | |
CHIKARA Like Phantoms, Forever
Nov 5th 2016 | Wani | def. (pin) | Oleg the Usurper | | |
CHIKARA The Black Goodbye
Sep 17th 2016 | Kobald & Kodama & Obariyon | def. (pin) | Heidi Lovelace & Oleg the Usurper & Ophidian | 6-person tag | |
CHIKARA King of Trios 2016 - Night 3
Sep 4th 2016 | Cassandra Miyagi & DASH Chisako & Meiko Satomura | def. | Oleg the Usurper & Princess Kimberlee & Super ThunderFrog | 6-person tag | |
CHIKARA King of Trios 2016 - Night 2
Sep 3rd 2016 | Oleg the Usurper & Princess Kimberlee & Super ThunderFrog | def. | Jazz & Lisa Marie Varon & Mickie James | 6-person tag | |
CHIKARA King of Trios 2016 - Night 1
Sep 2nd 2016 | Oleg the Usurper & Princess Kimberlee & Super ThunderFrog | def. (pin) | Cedric Alexander & Drew Gulak & Johnny Gargano | 6-person tag | |
 Smash (Canada)/CHIKARA Smash vs CHIKARA
Jul 24th 2016 | Evil Uno & Stu Grayson | def. | Dasher Hatfield & Oleg the Usurper | | |
CHIKARA When Nature Calls
Jul 23rd 2016 | Oleg the Usurper | def. | Officer Warren Barksdale | | |
CHIKARA Tightrope
Jun 11th 2016 | Jigsaw | def. (pin) | Oleg the Usurper | | |
CHIKARA The Distant Future
May 7th 2016 | Hallowicked | def. | Abominous Rex, Arctic Rescue Ant, Blind Rage, Brian Myers, Cheech, Dasher Hatfield, El Hijo del Ice Cream, Estonian ThunderFrog, Fire Ant, Frightmare, Gene Snitsky, Heidi Lovelace, Hermit Crab, Icarus, Ice Cream Jr., Jakob Hammermeier, Jervis Cottonbelly, Jigsaw, Juan Francisco de Coronado, Kobald, Lucas Calhoun, Mark Angelosetti, Missile Assault Man, Oleg the Usurper, Pinkie Sanchez, Prakash Sabar, Princess Kimberlee, Shane Storm, Steve Weiner, Touch Philips, Wani, Worker Ant II | Infinite Gauntlet | |
CHIKARA Disk
Apr 2nd 2016 | Frightmare & Hallowicked & Lucas Calhoun & Missile Assault Man | def. | Kobald & Kodama & Obariyon & Oleg the Usurper | 8-person tag | |
CHIKARA The New Batch
Mar 19th 2016 | Oleg the Usurper | def. (pin) | Blaster McMassive | | |
CHIKARA Evil Ways
Feb 28th 2016 | Oleg the Usurper & Princess Kimberlee | def. (pin) | Blaster McMassive & Flex Rumblecrunch | | |
CHIKARA Dead Man's Chest
Feb 27th 2016 | Kobald & Kodama & Obariyon & Oleg the Usurper | def. (pin) | Amasis & Fire Ant & Officer Warren Barksdale & Worker Ant II | 8-person tag | |
CHIKARA 5 Senses
Jan 30th 2016 | Princess Kimberlee (c) | draw (NC) | Oleg the Usurper | | CHIKARA Grand Championship
|
Oleg the Usurper during 2016