* A match contested [[https://www.youtube.com/watch?v=slY2ZCcJDZw&feature=related in slow motion!]] And the fans ''chanting along'' in slow motion!
* Wrestling/ChuckTaylor (yes, that is his name) [[https://www.youtube.com/watch?v=zOcjq4siu7A kills Soldier Ant with a "grenade"]]. Props to Soldier Ant and his HeroicSacrifice, as well.
* Ethan Page counters his opponent's move by [[https://www.youtube.com/watch?v=sCUzeZ8hlUM rewinding the match and using his knowledge of what he would do to counter him.]]
* The King of Trios 2008 tournament, which saw the surprising reemergence of Wrestling/{{Glacier}}, a throwback from WCW's later days; he was basically treated as another generic mid-carder after his heavily hyped debut in WCW, but when he took the King of Trios tournament by storm, he was more over there in ten seconds than he EVER was in WCW. Other Crowning Moments in the 2008 [=KoT=] include:
** The inclusion of Team WWF, consisting of Wrestling/{{Demolition}} and Wrestling/TheOneManGang. Specifically, the fact that One Man Gang and "Sweet and Sour" Larry Sweeney had [[https://www.youtube.com/watch?v=eTSr6iZd8xs one of Sweeney's trademark strut-offs, set to "Jive Soul Bro," the theme of Gang's old manager, Slick.]] Made even more awesome by the fact that thanks to a cosplaying fan, Gang had a hat resembling his old character Akeem's for the occasion.
** Egyptian time travelers Ophidian and Amasis (collectively known as The Osirian Portal) bringing in Mecha Mummy as their teammate, who busted out [[https://www.youtube.com/watch?v=4QLZL32f2Cs his own special counter]] to opponent Mike Quackenbush's trademark palm strikes.
* The 2009 King of Trios event's biggest Crowning Moment has to go to Gran Akuma, Icarus, and Chuck Taylor, aka Team FIST ([[FunWithAcronyms Friends In Similar Tights]]), for basically the ''entire weekend:''
** First, they beat the Death Match Kings (a trio that happened to include the current-day hardcore icon Wrestling/NecroButcher) in the opening round, despite being seemingly in over their heads.
** In the next round, they defeated the [=F1RST=] Family, a trio who had frequent standout matches in 2009 and 2008's Trios tournament; the team was headed by Arik Cannon, who is no stranger to going all the way in CHIKARA tourneys.
** In the semifinals, they took out The Future Is Now...which, despite the fact that FIST were the heels and TFIN were the faces, earned them a "Thank You FIST!" chant because the fans were just '''that sick''' of TFIN (and, specifically, Lince Dorado).
** And to cap it all off, they beat Team Uppercut (the all-star team of Wrestling/ClaudioCastagnoli, Wrestling/BryanDanielson, and Dave Taylor) in convincing fashion: first they killed what should have been a [=CMoA=] for Team Uppercut by rushing them at the entrance when they had come out to Danielson's classic [=ROH=] theme ("The Final Countdown" by Europe), then Chuck Taylor then ended up winning the match (and the tournament) for FIST by making Danielson, one of the best technical wrestlers on the planet and one of the biggest names in indy wrestling, '''''tap out.'''''
* Eddie Kingston delivers a warning: [[https://www.youtube.com/watch?v=h4h5Cu5WZcc "You can call me sick, but the world is cold. Bundle up."]] Especially awesome if you're not a fan of Lince Dorado - a category which, as the above example notes, [[TheScrappy a lot of CHIKARA fans happen to fall under.]]
* [[https://www.youtube.com/watch?v=Vz_I9mnpNPo Dragon Dragon, the only real dragon in professional wrestling]].
* Eddie Kingston's [[https://www.youtube.com/watch?v=c1AGjIQKxNE passionate speech about his match with Mike Quackenbush at "High Noon"]] may be the best promo he's ever delivered.
* The entire eight-man tag match at Under The Hood, which may just be the best-booked wrestling match of all time. So many underlying sub-plots, in-jokes and running gags, along with a few genuinely emotional moments, payoffs to storylines long-forgotten by many... just a sublime wrestling match which included more character development and storyline progression in one match than many WWE wrestlers are allowed in an entire storyline.
* The end of ''Three-Fisted Tales'', with the shocking return of Ares after four years in absentia and the huge riot that marked the formation of Wrestling/DieBruderschaftDesKreuzes, as [[https://www.youtube.com/watch?v=PAD7_K7soWs seen here]]. In fact, near the very end, someone in the crowd can be heard saying, "This is the greatest thing ever."
* The ''Rey de Voladores''[[note]]Spanish for "King of Flyers"[[/note]] qualifier from ''King of Trios 2009 Night II'' with [[Wrestling/SamiZayn El Generico]] vs. Kota Ibushi vs. Nick Jackson vs. Jigsaw, with tremendous action from all four guys, as seen [[https://www.youtube.com/watch?v=8XesuznnHaA here]].
* The re-emergence of CHIKARA at National Pro Wrestling Day 2014.
** The reveal of the then-leader of the Flood: Jimmy Jacobs.[[note]]Jacobs was busted down to TheDragon status three months later after the introduction of Deucalion.[[/note]]
** The Submission Squad, who had broken down on the side of the road (and in the same spot as the last time!), successfully arriving and declaring that the Flood had to go through them to destroy everything. They were beaten down, but they were saved by the timely arrival of Icarus and his allies.
** [=AssailANT=] finally winning the trust of the Colony, denying his former allies, and drawing the line.
** The reveal that Icarus' allies had infiltrated the Flood's ranks, dressed as Dr. Cube's henchmen, immediately after 17 was yanked through the entrance curtain by a cane.
** 3.0 and Archibald Peck rolling up [[Franchise/BackToTheFuture in a [=DeLorean=]]] to help run off the Flood.
** Archie and Mr. Touchdown burying the hatchet with a great big hug.
** CHIKARA's return on May 25th, 2014 (a date seen in the Ashes video "When?") being made official.
* Icarus wielding the late Estonian Thunderfrog's Hammer of War to end the onslaught of Deucalion.
* At the end of ''Sword of Destiny'', the Chicago crowd [[https://www.youtube.com/watch?v=gHuzMLos5Ig demanded one more match]]...and they got it!
* Princess Kimberlee's entire character arc, with her going from the spoiled manager of Knight Eye 4 The Pirate Guy to CHIKARA Grand Champion in the course of about two years.
* Team Sendai Girls (Cassandra Miyagi, Dash Chisako and Meiko Satomura) winning the King of trios 2016 to become the first queen of trios, doing so with 4 amazing matches.
* Thief Ant, Green Ant, and Fire Ant's King of trios 2018 run, first having to go against The Proteus Wheel, then in night 2 going 40 minutes with Team F.I.S.T. before being ambushed by The Raiders of the Beyond. For their next match Fire Ant wasn't even able to make it to the ring until 10 minutes in due to his injuries but when he did they were able to win quickly. In the finals they managed to take out The Order of the Nations to be crowned King of Trios, and finally officially become a new version of The Colony.
* Mike Quackenbush and Wrestling/ManamiToyota vs. The BDK (Claudio Castagnoli and Wrestling/SaraDelRey), in the second match of Toyota's American debut weekend (she defeated Wrestling/DaizeeHaze the night before at ''Eye to Eye''), at ''Through Savage Progress Cuts The Jungle Line'', September 19, 2010. Certainly the names alone should sell you on it, but, it absolutely delivers in every possible way. You can see it now [[https://www.youtube.com/watch?v=33uEiXg9_4w here]].
* Team CHIKARA[[note]][=UltraMantis=][=/=]Quack[=/=]Kingston[=/=]Jigsaw[=/=][=Hallowicked=][=/=]Icarus[=/=]STIGMA[=/=]Sweeney[[/note]]-BDK[[note]][=/=]Ares[=/=]Claudio[=/=]Tursas[=/=]Pinkie Sanchez[=/=]Donst[=/=]Sara Del Rey[=/=]Daizee[=/=]Delirious[[/note]] Torneo Cibernetico at ''The Dark Ciberknetico'', October 23, 2010. Amazing action from beginning to end that packs tons of history into a brisk 35 minutes and change. Plus, [[{{Tearjerker}} it's Larry Sweeney's last-ever CHIKARA appearance]].
* Oh gosh, Heidi Lovelace's [[https://www.youtube.com/watch?v=VOZ5s9WqCQE promo]] before her history-making all-female CHIKARA Grand Championship match with Princess Kimberlee at ''The Secret of the Ooze'', March 19, 2016, should have been enough to get her ranked up there with MICK FOLEY and TERRY FUNK as one of the all-time great talkers in wrestling history. The emotion is palpable as she realizes that she has to do what she doesn't want to do, hurt her friend, but "there is so much at stake tonight." The actual [[https://www.youtube.com/watch?v=4xozXN60MBI match]] is absolutely fantastic too, and the perfect match for Women's History Month.
** Heidi Lovelace [[https://www.youtube.com/watch?v=PGByqXoUb5o&t=1s defeating]] Missile Assault Ant in the Young Lions Cup final during the Pre-Show-A-Go-Go before ''Tomorrow Never Dies'', making her the first woman to win a title in CHIKARA.
* Ashley Vox's whole RoaringRampageOfRevenge throughout Season 18 against Merlok over his hurting her sister (Delmi Exo) and her friend (Jawsolyn) leading to her channeling the darkness within herself to become "The Queen of the Seven Seas" Oceanea and finally being able to [[https://www.youtube.com/watch?v=LgKfLNmahic&t=2s defeat]] Merlok at ''Closing Time'' on December 2, 2017.