After it was revealed that Kaye was a teacher, and the story was posted on news sites around the world, Kaye made a second appearance in WWE on the July 11, 2005 edition of WWE Raw in East Rutherford, New Jersey to face Kurt Angle once again. Kaye said his name was Matt Martel and that he was from New York but Angle recognized him as Matt Striker, and reminded the audience that Striker was the guy in the news who got fired from for being a wrestler and that Angle had defeated him before when Striker said he was from Philadelphia. Calling Striker "a liar" Angle finally decided to give him a second chance. In the 3:00 minute time limit match Angle defeated Striker for a second time, but Angle managed to make him tap out with only 1 second left on the clock. WWE signed him to a contract on July 12, 2005.
On July 18, 2005, Striker made a third appearance for WWE in Philadelphia, Pennsylvania, once again attempting to win the Olympic gold medal from Kurt Angle in his invitational. Striker this time said he was Matt Martel and that he was from Philadelphia. Once again exposing him to be a "big liar", Angle attacked and forced Striker/Martel to submit for a third time, though Martel did manage to get Angle in his Happy Monkey chokehold and hold him in it for nearly two minutes.
Striker made his official signed debut on an episode of Heat airing August 7, 2005, where he defeated Johnny Parisi. On September 28, 2005, Striker appeared on WWE Byte This! webcast show and did a less-than-flattering impression of Ultimate Warrior, including numerous references to steroids. He, Todd Grisham and Droz had several jokes at Warrior's expense, resulting in an edited version to be released on WWE's official website days later that takes a more light-hearted approach. This was due to Warrior releasing a paragraph-long statement, calling the host Grisham a "queer", and frequent contributor Droz (who was left a paraplegic by a wrestling accident) a "cripple".On October 21, 2005, Striker turned heel when he walked out on his tag team partner, Shelton Benjamin - in a match against Kerwin White and Nick Nemeth, only one week after Striker helped Benjamin fend off an attack from the pair. He would go on to release a promo on WWE.com referring to WWE as his school. Striker teamed with Kerwin White to defeat Val Venis and Shelton Benjamin on the Taboo Tuesday pre-show Heat, with Striker pinning Benjamin to obtain the victory.Striker's heel teacher gimmick had him hosting a segment called Matt Striker's Classroom on Raw, which was debuted on December 12, where he would insult the crowd about their family values and treat them as intellectual inferiors. The gimmick, which has been compared to that of Dean Douglas, often insinuates that many people in the arena are "smoking the pot" as one of the many insults. Shortly after, in a match that took place on December 18, Striker faced Lance Cade at a house show in Ft. Myers, Florida. During the match, Striker was thrown out of the ring by "Lancelot" (as Striker called him), landing horribly wrong on the floor, thus dislocating his shoulder and putting him out of action until January 23, 2006, when he continued his Classroom segments once again.
Striker would continue to host his segment during WWE.com Unlimited for several weeks. On February 21, 2006, Striker announced that he was in the then-latest edition of GQ Magazine. Striker would later return to defeat jobbers on Heat.
Striker would reappear on Raw on April 17 for another classroom segment where he claimed that "School is Cool". This brought out then baby-face, Carlito who took the teacher's apple and spat it in the face of Striker. Striker returned to Raw in-ring action on April 24, where he teamed up with Chris Masters and then-WWE Intercontinental Champion Shelton Benjamin to face Carlito, Rob Van Dam, and Charlie Haas in a six-man tag team match. Striker would end up on the losing end of the match when Rob Van Dam pinned Shelton Benjamin in the closing moments of the contest.
During Backlash, Striker would begin to feud with the (kayfabe) mentally impaired Eugene, after Eugene made an appearance on Matt Striker's Classroom during the PPV, and gave him a stunner. Striker gained some measure of revenge on Eugene the following night by hammering him in the back of the head with a dictionary while he was being interviewed. This feud would also involve a tweener Carlito, for a short while, who ended up attacking both Eugene and Striker after Eugene inadvertently caused Carlito to lose a match to Striker by Disqualification on the May 8 edition of Raw. The feud apparently ended when Eugene gained a mentor in Hacksaw Jim Duggan and finally was able to defeat Striker, after losing to him only two weeks before. After this match, Striker proceeded to smash Eugene's head on the steel ring steps. He fled to the back as Duggan approached him, however, Striker later defeated Duggan at a house show.
Afterwards, Striker would end up back on the web-show Heat, defeating jobbers. He made small appearances on Raw during June 2006, mainly on WWE Unlimited, but occasionally wrestling as well. During July, Striker would appear on Raw, occasionally teaming with Rob Conway to lose to the debuting Highlanders tag team. During these tag matches Striker would abandon Conway. This resulted in a match between the two on Heat, which Striker won.
Striker's final match on Raw was on July 31, where he was defeated in quick fashion by John Cena. This match came about as a result of Striker insulting Cena during one of his Classroom segments a week prior, claiming that then-WWE Champion Edge was greater than Cena.
At the end of August 2006, Striker would leave Raw to join WWE's revived ECW brand. Striker continued his Classroom segment on ECW, often only to be interrupted by The Sandman. During one such segment on September 5, 2006, however, Striker made a controversial remark that alluded to the death of Australian wildlife expert Steve Irwin, who had been killed by a stingray 36 hours earlier.
Striker made his in-ring debut on the September 19, 2006 edition of ECW, teaming up with Mike Knox and Test to face Tommy Dreamer, Sabu, and The Sandman. Despite Striker eliminating Sandman from the match after pushing him from the ring apron onto the ring barrier, he, Knox, and Test lost the match by disqualification due to Test pushing the referee.
Striker would continue his feud with the Sandman for the next few weeks, until Sandman came out victorious in a Singapore Cane on a Pole match on the October 17, 2006, edition of ECW. Striker lost the match by countout.
At the ECW December to Dismember pay-per-view, Striker faced Balls Mahoney in a "Striker's Rules" match, meaning no eye gouging, hair pulling, top rope attacks, or foul language. Despite the match being of his own creation, Striker was pinned by Mahoney. Striker would continue the feud with Mahoney until the December 19, 2006, edition of ECW, where Striker defeated Mahoney cleanly.
On February 6, 2007, Striker joined Mr. McMahon's New Breed stable and, with his stablemates, engaged in a feud with the ECW Originals. At WrestleMania 23, the New Breed was defeated by the ECW Originals in an 8 man tag. Tension began to appear between Elijah Burke and Striker after Striker and Marcus Cor Von were defeated by the debuting Major Brothers. Eventually, the New Breed would feud with the ECW Originals, CM Punk and the Major Brothers at the same time. At One Night Stand, Striker along with Marcus Cor Von and Elijah Burke lost to Tommy Dreamer, Sandman, and Punk in a Tables Match.
On June 26, 2007, he was a guest on Piper's Pit. Since it was his birthday, he asked Rowdy Roddy Piper to sing happy birthday to him. While singing, Piper threw a cake that was brought into the ring right into Striker's face. Striker was then chased from the ring by the Boogeyman, but Piper chucked him back into the ring where he was chokebombed and then fed worms. On July 10, 2007, Striker invited Boogeyman to the ring to apparently educate him on worms, only to bring out the debuting Big Daddy V (formerly known as Viscera on the Raw brand), who would attack Boogeyman and throw him through Striker's desk and chalkboard. Striker then acted as the manager of Big Daddy V, as well as the occasional manager of SmackDown! superstar Mark Henry. On April 11, 2008, he returned to in-ring action against Finlay. He lost by pinfall thanks to a few humorous distractions by Hornswoggle. On April 30, 2008 he was mandible clawed by Mick Foley on a segment of Matt Striker's Classroom on ECW. Striker used to host a weekly segment on WWE.com called "Best WWEek Worst WWEek", where he comments on which WWE superstars and other celebrities are having the best week or the worst week, and also reads out fans' emails. After 12 episodes, Striker announced an end to the segment citing time issues in regards to his duties as an announcer.
As part of the 2008 WWE Supplemental Draft, Striker was drafted back to the Raw brand. Once the SmackDown color commentator, Mick Foley, was storyline injured by Edge, however, Tazz moved over to SmackDown to fill in for Foley who actually left the WWE in real life and Striker remained on ECW to take over Tazz's duties as color commentator. He made his commentary debut on the August 5 episode of ECW and on August 17, 2008 at SummerSlam he called his first pay-per-view match (Matt Hardy vs. Mark Henry, which Hardy would win by DQ). Since then, Striker's commentating has been highly praised by fans and Striker and Todd Grisham even won the 2008 Slammy Award for Announce Team of the Year. On the April 7, 2009 episode of ECW, Grisham and Striker's commentary partnership came to an end when Grisham moved to the SmackDown brand, and Josh Mathews became the new play-by-play commentator. In addition to commentating on ECW on SyFy and ECW pay-per-view matches, Striker along with Mathews would represent the ECW brand on WWE Superstars every week starting with the inaugural episode on April 16, 2009. On October 27, 2009 it was announced that Striker would move from commentary on ECW to SmackDown, reuniting with Grisham. The move was made to help accommodate Jim Ross, who has been taking time off to deal with his recent Bell's palsy attack.