Jossed: After the BDK was formed, the fans expected that Crossbones would become the 8th member, due to 1) UltraMantis Black treating him with contempt while favoring Delirious, and 2) his conspicuous absence during the brawl when the BDK formed. Before the next show even happened, Pinkie Sanchez commented the theory out in a blog, pretty much indicating it wasn't going to happen. And of course it didn't - Lince Dorado was the 8th member.
Much of the BDK reveal in general was this, moreso than Crossbones as the 8th member; most notably, the idea that Carpenter Ant and Vökoder were both from the future due to their presence in a CHIKARA comic book set in the future was basically treated as the gospel by much of the fanbase, and Tim Donst and Pinkie Sanchez thoroughly mocked them for it after the fact.
Old Shame: The pre-2004 shows, which most everyone on the CHIKARA roster have referred to as varying degrees of 'bad'. Icarus in particular has said that he'll do everything he can to keep the match in which he lost the Ichabod Slayne mask from seeing the light of day.
Promoted Fanboy: A pre-Director of Fun Leonard F. Chikarason is very visible in the front row at many of the early 2004 shows.
In 2005, while CHIKARA and CZW were still co-running the Wrestle Factory, CHIKARA introduced a promotion for the school's "graduates" called NEXT, later renamed STF (Stars of The Future). It lasted ten shows, from NEXT: Genesis Point on April 7, 2005 to STF Monster Mash II on October 28, 2006.