After a short break during the winter months (establishing CHIKARA’s seasonal format), Season Two began on March 8th, 2003, at the Thirteenth Show. Blind Rage, having vanquished partner-turned-enemy Ichabod Slayne in a Lucha de Apuesta (hair vs. mask) match at the Season One finale, turned his ire towards DJ Skittlez in a losing effort, commencing a feud that would rage throughout much of the Season. Hallowicked defeated Private Eye, CM Punk was defeated by Don Montoya, and Gran Akuma defeated Mitch Ryder. The main event was a Trios match, in which Mike Quackenbush, Mister ZERO, and UltraMantis defeated the Toxic Trio of Jigsaw and the Wild Cards (Eddie Kingston and BlackJack Marciano). Later in the month at the fourteenth show, a Double Jeopardy Battle Royal saw ZERO and UltraMantis be put in a match later in the show, which was declared a double disqualification due to the interference of the Wild Cards, who had participated in the battle royal as well. Kingston defeated Private Eye later in the night. The former Ichabod Slayne, now known as Icarus, re-debuted during this show, defeating Hallowicked. The main event saw the debut of Rorschach, as he, Jigsaw, and Blind Rage were defeated by Quackenbush, Akuma, and DJ Skittlez. Jigsaw and Rorschach would soon form a team known as the Conundrum.
UltraZERO and the Wild Cards clashed once again as Marciano and Kingston met ZERO and UltraMantis in separate singles matches at the Fifteenth Show the next month, with Kingston defeating UltraMantis and the match between ZERO and Marciano ending in a double disqualification. The feud that had ignited between the two teams was nowhere near finished. At the next two shows the two teams would face each other during a pair of Trios matches (ZERO teaming with Quackenbush and Akuma the first match and UltraZERO teaming with Quackenbush the second to face the Wild Cards and Rorschach), with the tecnico team defeating their rivals each time. In revenge, after the latter match, Kingston locked UltraMantis in the Kondo Clutch and refused to let go, injuring him. Also during the seventeenth show, Hallowicked made his first successful defense of the Young Lions Cup during the Season (and second overall) when he defeated Icarus, and the feud between Blind Rage and DJ Skittlez continued as the former defeated the latter.
UltraMantis sought revenge against the Wild Cards at the eighteenth show in May, interfering in a tag match and causing a double disqualification. DJ Skittlez was once again defeated by Blind Rage, though not without controversy as the referee failed to notice Skittlez’ foot on the bottom rope. The feud between both men came to a head at the very first Aniversario show, as Skittlez defeated Rage in a match where the winner would be able to choose the loser’s entrance music. Amusingly, Skittlez selected “Conga” by the Miami Sound Machine as Rage’s new entrance music. UltraZERO and the Wild Cards met in another match as they took part in a main event ten man tag team match that also included Quackenbush, Akuma, Icarus, Hallowicked, Jigsaw, and Rorschach. The tecnicos defeated the rudos to close out the show. This match is also notable for being the first time the future Team F.I.S.T. (short for Friends In Similar Tights) had teamed together.
Unfortunately, the triumph of the technico team did not settle the issue between the two teams, as the next month at You Be The Booker!, they met once again, this time in an I Quit match (won by the Wild Cards), then one last time during the very first Tag World Grand Prix in July (with UltraZERO victorious). Team F.I.S.T. made their pairing official, entering the Grand Prix as well, though they were defeated in the second round by eventual winners Blind Rage and Hallowicked. Claudio Castagnoli made his first appearance in CHIKARA during the tournament, bringing with him a figure who would become very important in later Seasons: Ares. They met the Superfriends (Quackenbush and Chris Hero) during the tournament, resulting in a thirty minute draw which eliminated both teams. The finals of the tournament actually took place later in the month with the Night Shift winning before injuring ZERO.
Having moved on from UltraZERO, the Wild Cards next engaged Team FIST, starting a feud that would last through the rest of the Season and into the next. In separate singles matches at the second half of the Tag World Grand Prix, Icarus and Akuma respectively defeated Marciano and Kingston, then were defeated by them in further singles matches at the Twenty-Third Show. UltraMantis sought revenge on behalf of ZERO, defeating Hallowicked at the Twenty-Third Show but later failing to unseat him for the Young Lions Cup at the Twenty-Fourth Show. Also at that event, Team FIST teamed with Quackenbush to take on and defeat the Toxic Trio in a six man tag two out of three falls match, and Rorschach defeated Jolly Roger to qualify for the following Season’s Young Lions Cup tournament. At the Season finale, The International Invasion of International Invaders, Jolly Roger won entrance into the Young Lions Cup tournament (though he would have a rematch for entry in the following Season); ZERO won #1 contendership for the Young Lions Cup in a battle royal, but was unable to unseat Hallowicked; foreshadowing one of the biggest rudo turns in CHIKARA’s history for the following Season, Blind Rage revealed that the Night Shift had become a Trio again while UltraMantis began to display rudo behavior towards ZERO; the Wild Cards ambushed Team F.I.S.T., leading to a no disqualification match that was very nearly a handicap match due to Akuma being injured, the match (won by the Wild Cards) ensuring that their feud would continue into the following Season; and in the main event, Quackenbush defeated Skayde for the AULL/IPW Mexican Middleweight Championship, which would become one of the titles that made up Quackenbush’s International Crown the following Season.
This was not meant to be the Season finale, but sudden and unforeseen issues regarding the venue CHIKARA events were regularly taking place in ended the Season early, forcing a change in location before the next Season could begin.