The promotion held multiple live events per month, with the majority taking place at the Chikara Wrestle Factory school.

The first show on May 25, 2002, featured not only the Wrestle Factory students and head trainers, but several other independent wrestlers, including Don Montoya, CM Punk, Colt Cabana, Chris Hero, Love Bug, Marshal Law, and Blind Rage.

The main event of the first show featured Quackenbush and Youth joined by Don Montoya as the Black T-shirt Squad defeat the Gold Bond Mafia of Chris Hero, CM Punk, and Colt Cabana.

In the early days, Blind Rage, Hallowicked, and Ichabod Slayne formed a stable known as the Night Shift, which became the top group of rudos (or heels) in the promotion.

The first show in St. John's saw the Wildcards (Eddie Kingston and BlackJack Marciano), Gran Akuma, D. J. Skittlez, Melvin Snodgrass and Lester Crabtree debut, and shortly after, they were joined by Wrestle Factory graduates Jigsaw and Bryce Remsburg.

Hallowicked defeated Mister Zero to win the inaugural tournament, becoming the first-ever Young Lions Cup Champion in the process.

[4] Throughout the years, Chikara has also worked with several Japanese promotions in bringing their talent over to the United States, including Dragon Gate,[5] Ice Ribbon,[6] JWP Joshi Puroresu,[7] and Sendai Girls' Pro Wrestling.

[9] In December 2011, Chikara partnered with numerous Japanese promotion to hold the three-day-long JoshiMania event, which featured some of the biggest names in joshi puroresu.

[7] Wrestlers such as Aja Kong, Dick Togo, The Great Sasuke, Jinsei Shinzaki, Kana, Kaori Yoneyama, Kota Ibushi, Manami Toyota, and Mayumi Ozaki have made rare American appearances for Chikara.

[15][16] In February 2012, Chikara launched their first ever web comic, written by Joey Esposito and drawn by Alex Cormack, telling the secret origin of Frightmare.

On April 6, 2013, Chikara took part in WrestleCon, held during the WrestleMania 29 weekend in Secaucus, New Jersey, holding an event, which again broke the promotion's attendance record.

[17] On June 2, 2013, Chikara ran an angle at the conclusion of their fourth iPPV, Aniversario: Never Compromise, where the event was shut down by Director of Fun Wink Vavasseur.

[21][22][23] In October 2013, Viz Media acquired rights to 26 Chikara events, which would start airing on their Neon Alley digital service on Sundays as part of the new fall lineup.

[26] In April 2015, Chikara made its debut in the United Kingdom with a four-show tour held across England and Wales[27] and launched Chikaratopia, a streaming service featuring past events.

[28] That same year on July 29, the promotion launched a new weekly program, entitled Journey Into Chikara, which would air live on both Chikaratopia and YouTube.

[34] As of now, training to prospective professional wrestlers, managers, valets, and referees in Northeastern Philadelphia, Pennsylvania[2] is offered in all styles of pro wrestling, including lucha libre, puroresu, Lancashire, and catch, among others.