The Spirit Squad made their first appearances in WWE at house shows and in dark matches. On January 23, 2006, they had their television debut, when they appeared on Raw and helped Jonathan Coachman win a Royal Rumble qualifying match against Jerry "The King" Lawler by performing cheers for Coachman and distracting Lawler. In subsequent weeks, the team was hired by several wrestlers to perform cheers for them.
They eventually became a part of the ongoing feud between WWE chairman Vince McMahon and Shawn Michaels. The villainous McMahon ordered the Squad to perform disrespectful cheers about Michaels, attack him on numerous occasions, and face him in multiple handicap matches.
While involved in the Michaels-McMahon feud, they also continued wrestling in the tag team division, and on the April 3 episode of Raw, won the World Tag Team Championship when Kenny and Mikey – with outside help from the other three Squad members – defeated Big Show and Kane. After winning the championship, an "executive edict" was declared stating that all five members were recognized as the champions, with any two members allowed to defend the championship at once under the Freebird Rule.
On May 1, the night after the Backlash pay-per-view, the five members of the Spirit Squad were jointly named "Co-General Managers" of Raw. During the night, after drawing "spirit straws", they placed Kenny into a title match with WWE Champion John Cena. Before the match, they ordered play-by-play analyst Joey Styles in their office to instruct him on how to call Kenny's upcoming win (which never did come to pass), instructing him to do it "with spirit" or they would force him to call all of the following Raw episodes while wearing a female cheerleading uniform. This led to Styles confronting color commentator Jerry Lawler and eventually quitting the show in a promo. Kenny lost the match after special referee Triple H, who was conspiring with the Squad, walked out on the match.
Three weeks later, on Raw, Vince McMahon signed another handicap match pitting the Spirit Squad against Shawn Michaels. The match never started, however, because the Spirit Squad attacked Michaels, ripping apart his ring attire and, in storyline, shattering his knee with a steel chair. McMahon then called Triple H to the ring to attack Michaels with a sledgehammer, however, Kenny snatched the sledgehammer away, disrespecting Triple H, which led to him attacking the group.
Triple H and Shawn Michaels revived D-Generation X (DX) and as a team began a feud with the Spirit Squad. DX played various sophomoric pranks on the Squad and the McMahons (Vince and his son Shane), including DX dumping green slime onto the group and embarrassing the team afterwards, by defeating them, and dumping feces on the Spirit Squad and the McMahons. DX defeated the Spirit Squad in handicap tag matches at Vengeance, and scoring a clean sweep in an elimination handicap match at Saturday Night's Main Event XXXIII.
At the same time as their feud with DX and their alignment with McMahon, the team also wrestled other teams in Raw's tag team division over their World Tag Team Championship. The Squad successfully defended the championship against the teams of Jim Duggan and Eugene, Charlie Haas and Viscera, and Snitsky and Val Venis before entering a lengthy feud with The Highlanders. They eventually defeated The Highlanders to retain the titles at the Unforgiven pay-per-view.
At the end of September and beginning of October, the Squad as a whole began a losing streak, with separate members losing singles matches to Ric Flair on consecutive episodes of Raw. After Johnny and Mikey lost to the debuting Cryme Tyme on October 16, Kenny started yelling at the other members of the Spirit Squad in the ring and walked off shouting "I'm tired of losing". Tensions further escalated the following week, when the Spirit Squad lost to Cryme Tyme for the second consecutive week. After the defeat, Kenny attacked Mikey, then announced he would defeat Flair, since no other member of the group could do it. Later on in the night, he was successful, with help from the rest of the Squad, despite Flair bringing a number of fellow "Legends" (Dusty Rhodes, Sgt. Slaughter, and "Rowdy" Roddy Piper) to the ring with him to even the odds. It was then decided that Flair and one of those legends, of the fans choosing, would wrestle the Squad at Cyber Sunday for the World Tag Team Championship. At Cyber Sunday, the fans chose Piper and he and Flair defeated Kenny and Mikey to win the title. At Survivor Series, The Squad (with Mitch) went on to face the legends consisting of captain Ric Flair, Sgt. Slaughter, Dusty Rhodes, and Ron Simmons (with Arn Anderson) in a losing effort.
The group disbanded on the November 27 episode of Raw, when they were defeated in a five-on-three handicap match by DX and Flair. In a backstage segment later that night, DX placed all members into a crate and shipped them away.
After the breakup, Kenny emerged as the only member to remain on WWE television, gaining the last name "Dykstra" and continuing the feud with Flair that led to the Spirit Squad's break up.
In late 2016, Mikey and Kenny returned to WWE for a short storyline with Dolph Ziggler (formerly Nicky in the Spirit Squad). On October 4, on SmackDown, they taunted Ziggler about his time in the Spirit Squad, before attacking him at the behest of the Intercontinental Champion The Miz and Maryse. Five days later, at the No Mercy pay-per-view, they attempted to distract Ziggler in his career versus title match against The Miz, but were unsuccessful. On the October 11 episode of SmackDown, Mikey and Kenny faced Ziggler in a two-on-one handicap match; Ziggler won but was attacked by The Miz before being saved by Rhyno and Heath Slater. This led to a six-man tag team match the following week, which Mikey, Kenny, and The Miz won. Mikey and Kenny unsuccessfully challenged Slater and Rhyno for the WWE SmackDown Tag Team Championship on October 25. They appeared throughout November in tag team matches, before disappearing off television once again.