Cole came to the World Wrestling Federation in mid-1997. He provided voice-overs for promotional videos and later became the host of LiveWire show alongside Jim Cornette. Cole first appeared on screen at SummerSlam, and replaced Todd Pettengill as a backstage interviewer, who left the WWF after the event. In late 1997, Cole became one of the three announcers for the first hour of Monday Night Raw, alongside Jim Ross and Kevin Kelly. Eventually Cole was permanently replaced by Jerry Lawler later in the year. In 1999, Cole became the regular play-by-play announcer for Monday Night Raw subbing for Jim Ross when Ross was devastated by Bell's palsy.
When the promotion's new SmackDown! television program debuted later that year, Cole was chosen to be the show's play-by-play announcer. Originally his broadcast partner was Jerry "The King" Lawler, but when Lawler briefly left the WWF, he was replaced by Cole's Heat broadcast partner Tazz shortly before the WWF vs. Alliance invasion storyline. Cole also had a stint doing commentary on SmackDown!'s former sister show WWE Velocity.
Cole called play-by-play at the 2006 Royal Rumble match because Ross, who had commentated the last two Royal Rumble matches with Tazz, had been "fired" in the storylines and replaced by former ECW play-by-play man Joey Styles, reuniting the original SmackDown! team of Cole and Lawler.
On the June 9 episode of SmackDown!, Cole's broadcast partner Tazz left from SmackDown to ECW on SciFi, leaving Cole at that moment without a broadcast partner. At ECW One Night Stand 2006, John "Bradshaw" Layfield announced he would replace Tazz as color commentator. This proved true five days later when he appeared on that week's episode of SmackDown! as Cole's new broadcast partner. After JBL left the broadcast booth and returned to wrestling action on Raw, Jonathan Coachman became Cole's new partner on January 4, 2008. Coachman was then replaced by Mick Foley beginning at Backlash on April 27, 2008.
As a part of the 2008 WWE Draft, Cole was drafted to the Raw brand as Jim Ross was drafted to the SmackDown brand. This effectively ended Cole's near 10 year run as play-by-play commentator on Smackdown in which he called every episode except for two. (The two episodes were the series premiere and the 9/11 Tribute show, both of which were called by Ross.) On the July 7, 2008 episode of Raw, Cole was attacked by Kane. He repeatedly asked Cole "Is he alive or dead?" before Cole was saved by Jerry Lawler. Cole made his in-ring debut as Lawler's partner against the tag team of Cody Rhodes and Ted DiBiase; a match for the World Tag Team Championship. Cole and Lawler lost after Cole inadvertently tagged himself in, and was quickly pinned by Rhodes after a lariat. On the December 14, 2009 episode of Raw, which was the 2009 Slammy Awards, Cole won The "Oh My God" Moment of the Year award for vomiting on Chris Jericho at SmackDown's 10th Anniversary show on October 2.
Cole became the color commentator for WWE NXT when the show debuted on February 23, 2010. Cole practically turned heel when he began showing signs of arrogance & cockiness towards face wrestlers and WWE fans alike. During his recent turn, he began to belittle certain rookies on the show, mainly Daniel Bryan. Cole began showing a liking to The Miz, who was Bryan's pro on that season, and who was becoming a significant heel on Raw. On the May 18 episode of WWE NXT, Bryan attacked Cole as a result of Cole's comments to him over the preceding weeks. The following week, Cole called Bryan out and demanded an apology from him, or else he would sue him for the assault. Bryan insulted Cole instead. Cole retaliated by calling Bryan a "loser" and slapping him, which caused Bryan to be restrained by security as Cole left the ring.
After his rivalry ended with Bryan, Cole would begin to belittle on other rookies from other seasons of the show. In the second season of WWE NXT, Cole would do this to Kaval and in the third season with A.J., calling them all "internet darlings". During third season of WWE NXT, Cole would criticize the who competition after a challenge, which required him to ring a gong, where he then walked out, "quitting" the show. The following week, Cole would return half way through the show, returning to the show. In the fourth season of WWE NXT, Cole would be replaced by Todd Grisham, but would make an appearance on the December 28 episode of WWE NXT, helping Brodus Clay in a talent competition.
On the June 21, 2010 episode of Raw, Cole was made the official spokesman for the Anonymous Raw General Manager, where he had to address the crowd what he had sent to him by e-mail. Cole would then debut his new catchphrase, "and I quote....", before reading each e-mail. On the October 1 episode of SmackDown, Cole returned to the show to join Matt Striker and Todd Grisham on commentary. On that same episode, Cole told Striker and Grisham that the reason he was on the show was that he was the new "Voice of the WWE" and that he should be on all WWE shows.
On the November 29, 2010 episode of Raw, Cole interfered in a Tables, Ladders & Chairs match for the WWE Championship between Lawler and The Miz, costing Lawler the match and helping Miz retain his title. A week later, Cole apologized, only to take it back and demand one from Lawler. After Lawler threatened to attack Cole, the anonymous Raw General Manager issued a "cease and desist" order, which barred any physicality between them and that if either of them violated the order, that individual would have their contract terminated immediately.
Cole continued to argue with Lawler on commentary, telling him he was "stealing the spotlight" and to "stop putting his nose in other people's business". After Lawler unsuccessfully challenged for the WWE Championship again at Elimination Chamber, Cole interviewed him about his match on the following Raw. When Cole mentioned Lawler's recently deceased mother, Lawler stole the microphone from Cole and challenged him to a match at WrestleMania XXVII. Cole responded by throwing water into Lawler's face and then running backstage.
A week later, Cole accepted Lawler's challenge to a match at WrestleMania, on the conditions that he could have his own personal trainer at ringside with him and if he could choose the special guest referee for the match. Cole then revealed his trainer to be Jack Swagger. On the March 7, 2011 episode of Raw, Cole announced that he had chosen John "Bradshaw" Layfield (JBL) as the referee for the match, but before he could sign the contract, Stone Cold Steve Austin interrupted and delivered a Stone Cold Stunner to JBL, and then signed the contract himself. Beginning on the March 14, 2011 episode of Raw, Cole began announcing both Raw and SmackDown inside a glass booth which he called the "Cole Mine". Later that night, Cole invited Brian Christopher, Lawler's son, to the ring to reveal some dirt about Lawler. Christopher confronted his father and told him he was ashamed to use the name "Lawler" and accused him of being absent from most of his life. Jim Ross then interrupted and confronted Cole. Jack Swagger attacked Ross and put him in an Ankle Lock. Cole followed suit with an Ankle Lock of his own. During following weeks he criticized the divas saying they should not be in WWE.
At WrestleMania, Lawler won the match using the Ankle Lock submission hold. While celebrating his victory with Stone Cold, the anonymous Raw General Manager reversed the decision, due to Stone Cold physically getting involved in the match by pushing Cole, making Cole the winner by disqualification. A month later at Extreme Rules, Cole teamed with Swagger to defeat Jim Ross and Lawler in a Country Whipping match. Lawler challenged Cole to one last match at Over The Limit. Cole initially declined, but Swagger was provoked into agreeing to the match on Cole's behalf.
A week later, Cole announced that the match would be a "Kiss My Foot" match. During the signing, Cole and Swagger's alliance ended when Cole insulted Swagger, causing him to walk out on Cole, who then tried to beg Lawler for forgiveness. At Over The Limit the pay-per-view, Lawler defeated Cole. After the match, Eve and Jim Ross would come out and get their retribution on Cole. Eve delivered her signature moonsault to Cole and Jim Ross covered his face in barbecue sauce. Bret "The Hitman" Hart would then return and put Cole in his signature submission move, the Sharpshooter, to help Lawler make Cole kiss Lawler's foot.
The following night on Raw, Cole made an apology to the fans and Lawler, which Lawler accepted. Cole continued to favor most villains and question the actions of the fan favorites to regain control in matches.
On the May 30, 2011 episode of Raw, during an in-ring interview with Alex Riley, Cole would insult him, which resulted in Riley pushing Cole, leading The Miz to attack Riley from behind, with the two then beginning to brawl. On the June 20 episode of Raw, Cole was voted as the opponent for Vickie Guerrero in a dance-off, hosted by Matt Striker, with Cole winning the contest from receiving the most boos from the crowd. On the July 25 episode of Raw, after Triple H announced the return of Jim Ross to commentary, Cole would protest to Triple H about it, where Triple H gave Cole the choice to stay or quit. After Cole decided to stay, Triple H would place Cole in a match against Zack Ryder; a match which Cole lost quickly.
On the October 17, 2011 episode of Raw, Cole and Alberto Del Rio lost a tag team match to John Cena and longtime Raw announcer Jim Ross. This prompted Cole to challenge Ross to the "Michael Cole Challenge" (a series of three contests) the following week; Cole said that if Ross won each challenge, Cole would quit his job. The two met on November 14 -- the "challenge" had been postponed twice due to Ross being (legit) ill -- and after Ross won the first two challenges (arm wrestling and dancing), Cole then declared the third contest was who weighed less, which Cole won. After Ross was "fired," CM Punk came out and attacked Cole, putting him in the Anaconda Vice submission hold and injuring his arm; Cole vowed revenge and said he would sue Punk for injuring him.
Cole reignited his NXT rivalry with Daniel Bryan on the November 25, 2011 episode of SmackDown, in response to Bryan cashing in his "Money in the Bank" contract and pinning an incapacitated the Big Show to win the World Heavyweight Championship; Cole called Bryan a "hypocrite" who wouldn't stay true to his beliefs. Several weeks later, Cole began taunting Bryan over his feud with Henry; when Bryan went to confront Cole, Cody Rhodes (who was providing color commentary) attacked Bryan.
On January 29, 2012, Cole was a surprise entry in the 2012 Royal Rumble match. He was eliminated by Lawler and Booker T and the returning Kharma. On the June 4, 2012 episode of Raw Cole was put in a match with John Cena which he lost, and was forced to make an apology for all of his wrongdoings.
On the July 9 episode of Raw, Cole against Jerry "The King" Lawler in a WrestleMania XXVII rematch, which he quickly lost, the anonymous Raw General Manager reversed the decision and Cole won by disqualification following interference by Booker T. Santino Marella came out to reveal that Hornswoggle as the anonymous Raw General Manager who was pulled out hiding underneath the ring.
Cole was lauded for his handling of his fellow commentary partner Jerry Lawler's legitimate on-air heart attack on the September 10 episode of Raw. Cole, a long time heel commentator, provided updates to television viewers on Jerry Lawler's condition throughout the episode and was described as "classy and professional" for his handling of the emergency. Since then, Cole has made a slow transition to being a face once again for the first time since 2010, favoring the face wrestlers as well as being cheered for his professionalism for Jerry Lawler, while JBL, who filled in for Lawler during his recovery, gradually went on a heel turn and replaced Coles' role after Lawler recovered. Despite his face turn, Cole has maintained many of his same gimmick qualities, though while conversely cheering on face wrestlers as opposed to heel wrestlers. Since Monday, April 1, 2013, John "Bradshaw" Layfield has done commentary for Raw alongside Cole and Lawler. Since his joining, Cole and JBL have taken to sharp, contentious exchanges with regards to the Alberto Del Rio-Jack Swagger feud in particular. The duo also debuted a webshow called the JBL & Cole Show airing every Sunday.
On the March 30, 2015 episode of Raw, Cole, along with JBL and Booker T, were attacked by Brock Lesnar after Seth Rollins refused Lesnar his WWE World Heavyweight Championship rematch. Cole was also F-5'ed by Lesnar in the ring.