Season Three began on March 20th, 2004, at Kids Eat Free On Tuesdays. The very first match featured the debut of Shane Storm, who would go on to become a semi-important figure in later Seasons, as he teamed with Private Eye to defeat Darkness Crabtree and Phantasmo. Mike Quackenbush held a gauntlet match to determine a #1 contender to the four titles he held (dubbed the International Crown), which, interestingly enough, were all from other promotions. This would not be the only time titles from other promotions would be defended in CHIKARA, or even during this very Season. The gauntlet was won by Jigsaw, who defeated DJ Skittlez (who had upset UltraMantis in the match before, prompting UltraMantis to shove him to the floor in anger) in the final match. Jolly Roger qualified for the Young Lions Cup tournament by defeating Rorschach, and the feud between the Wild Cards (Eddie Kingston and BlackJack Marciano) and Team F.I.S.T. (Gran Akuma and Icarus) continued, as they, along with Hallowicked and Quackenbush on each respective team, main evented the show in an elimination Trios match. Akuma would come away the sole survivor, though Kingston would make his child cry afterward, which was an unforgiveable offense.
The next month, at Pick Up or Delivery, Cavalier Jones, a member of the Board of Directors, presented Jolly Roger with a medal indicating his entry into the Young Lions Cup tournament, which would later be stolen by Darkness Crabtree. The Wild Cards and Team F.I.S.T. continued their war, bringing Quackenbush and Jigsaw into it as their match for the International Crown was interrupted. While Cavalier Jones threatened to suspend the Wild Cards, Quackenbush offered another solution: a Trios Lucha de Apuesta (Icarus’ hair, Akuma’s mask, and the International Crown versus the Wild Cards’ hair and Jigsaw’s mask), set for Aniversario. UltraMantis, having already displayed rudo behavior at the Season opener, backstabbed his long time partner Mister ZERO during a tag match against Joker and Sabian. After verbally abusing his now-former tag partner and claiming that he was sick of the human species as a whole, he removed a black mask from ZERO’s briefcase and donned it, declaring the birth of one of CHIKARA’s cornerstones: UltraMantis Black.
Aniversario soon came. Storm was presented with a Young Lions Cup medal, though he would take some verbal abuse from a newly-rudo Cavalier Jones, who had aligned himself with the Toxic Trio (the Wild Cards and Jigsaw). Jones’ job was placed on the line in the main, replacing Jigsaw’s mask as one of the stipulations. Jolly Roger reclaimed his Young Lions Cup medal from Darkness Crabtree. Blind Rage declared his retirement after defeating DJ Skittlez, though this would actually last less than a year. The Dark Breed would form, as UltraMantis Black teamed with Hallowicked to defeat ZERO and Storm. In the main event Lucha de Apuesta, the Trio of Team F.I.S.T. and Quackenbush defeated the Toxic Trio with Akuma making Kingston submit, costing Jones his job as well as the Wild Cards their hair. Many tecnicos gathered afterward to watch the Wild Cards get their heads shaved.
It was soon time for the second annual Young Lions Cup tournament, which attracted many young competitors as it had back in Season One. Highlights included the members of two separate tag teams meeting within the tournament as opponents (Jigsaw and Rorschach in the opening round and Kingston and Marciano in the quarterfinals) and an additional qualifying match made on the second day due to the sudden absence of Jay Lethal. His replacement, Chris Hero, made it all the way to the semi-finals before being knocked out of the tournament by “Sweet ‘N’ Sour” Larry Sweeney. The tournament was won by Sweeney, who defeated Jigsaw in the finals. This win gave rise to the formation of Sweet ‘N’ Sour International with his minions the ShareCropper, Crossbones, Mano Metalico, Spyrazul, Mobius, and Flex Fenom.
Sweeney’s win over Jigsaw began a rivalry that would last for the remainder of the Season. After an eight-man tag at Retribution Rumble of Revenge and Rumble to Remember (during which the absence of Quackenbush was pointed out, which would begin to foreshadow a related event later in the Season), Sweeney proposed a best of seven between Sweet ‘N’ Sour International and a team led by Jigsaw to see who the best really was. The odds were soon upped by both Jigsaw and Sweeney, putting a future match between the two at stake in the series as well. At 77, the show before the series began, Jigsaw would defeat Sweeney in a Trios contest, which also saw the full-time debut of Claudio Castagnoli, who had previously competed at the 2003 Tag World Grand Prix. Also at 77, the Wild Cards continued the trend of non-CHIKARA titles being defended at CHIKARA shows, defending the IWA Mid-South tag team championship, which they had won at the 2004 Ted Petty Invitational. They would continue to defend them for the rest of the Season, even clashing one last time with their long-time rivals, Team F.I.S.T.
The best of seven series commenced at Beware of Barely Badd Blasts and/or Blood Brawls on the Beach. Jigsaw recruited Team F.I.S.T., Skittlez, Sabian, Jolly Roger, ZERO, and Storm, while Sweeney fielded his Sweet ‘N’ Sour International (bolstered by the addition of Jigsaw’s ex-tag team partner Rorschach), Castagnoli (replacing Mobius), and the Dark Breed. Once again, Sweeney made reference to Quackenbush’s absence. In a 4-3 result in favor of CHIKARA (with Akuma taking the final victory against Mano Metalico), Jigsaw/Sweeney became the show’s main event. Jigsaw achieved victory over his hated rival, but Sweeney was quick to remind him that it was not for the Young Lions Cup. As he had gone through sixteen men to attain the Cup, he believed Jigsaw should have to as well to get a shot at it, the idea of which gave rise to a yearly CHIKARA tradition, the Torneo Cibernetico. Before the Cibernetico, Jigsaw and Sweeney clashed one more time in an Atomicos match at More Songs About Buildings and Food, which saw Sweeney pin Jigsaw.
The Cibernetico Cometh, and for a third time, Sweeney pointed out Quackenbush’s absence from the proceedings. All his references to Quackenbush would soon come back to haunt him. A long, thrilling match came down to Jigsaw against Sweeney, Rorschach, and Spyrazul. The three-on-one advantage pleased Sweeney, who would begin to celebrate his impending victory. Unfortunately for him, this victory was not to be. Behind his back, Spyrazul turned on Rorschach, causing his elimination, before unmasking to reveal that he was Quackenbush in disguise. Throwing his mask at Sweeney, he wished Jigsaw well and voluntarily exited the match, making it one-on-one. Not long after that, Jigsaw secured victory and his shot at the Young Lions Cup at the Season finale, Fear of Music.
Jigsaw made good on his shot. Sweeney came out wearing a sling, claiming he had injured his arm putting on his robe, and that he would have to forfeit the match. He had seen that this had worked for Sabian earlier in the show and had tried to use it for himself. While it didn’t work, he was able to attack his opponent from behind. After a hard-fought match which nearly saw the interference of Rorschach before Quackenbush (who had fended off Sweeney’s interference in his match earlier in the show) cut him off, Jigsaw defeated Sweeney to win the Young Lions Cup, a moment that was celebrated by tecnicos hoisting him onto their shoulders. The next night, at a rare post-season event, In Memory Of Adam Mills…, Jigsaw made his sole defense of the Season, defeating Marciano.