Cole came to the World Wrestling Federation in mid-1997 after being recommended to company officials by Todd Pettengill. He provided voice-overs for promotional videos and later became the host of the LiveWire show alongside Jim Cornette. Cole first appeared on screen on the June 30, 1997 episode of Raw is War, interviewing The Legion of Doom and replaced Todd Pettengill as a backstage interviewer after SummerSlam. 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 in mid-1998. 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 Lawler, but when Lawler briefly left the WWF, he was replaced by Cole's WWE Sunday Night Heat broadcast partner Tazz shortly before the WWF vs. WCW/ECW invasion storyline. Cole also had a stint doing commentary on SmackDown!'s former sister show WWE Velocity.
As an announcer, Cole was rarely involved in storylines; however, he has had minor roles in storylines involving Heidenreich, Stephanie McMahon, Vito, and D-Generation X (Triple H, Shawn Michaels, Chyna, and Rick Rude). He also appeared in the Taxi Driver parody trailer in promotion of WrestleMania 21.
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 (kayfabe) "fired" 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, leaving Cole at that moment without a broadcast partner. At ECW One Night Stand, 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. At 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 was the lead commentator for WWE NXT for its first three seasons. During the first season in 2010, Cole began showing signs of arrogance and cockiness towards face wrestlers and WWE fans alike, turning heel for the first time in his career. He also began to belittle Daniel Bryan and took a liking to The Miz, leading to confrontations with Bryan throughout the season. Meanwhile on the Raw brand, Cole was made the official spokesman for the Anonymous Raw General Manager beginning on June 21, 2010. Cole returned to SmackDown to join Matt Striker and Todd Grisham on commentary beginning on October 1, and branded himself the "Voice of the WWE", stating that he should be on all WWE shows going forward.
On the November 29, 2010 episode of Raw, Cole interfered in a Tables, Ladders and Chairs match for the WWE Championship between Jerry Lawler and The Miz, costing Lawler the match and helping Miz retain his title. This began a feud with Lawler that built towards a match at WrestleMania XXVII. During this time, Cole revealed that Jack Swagger was his personal trainer and he antagonized Lawler with antics such as making light of his mother's death and inviting his son, Brian Lawler, to air family secrets. At WrestleMania, special referee Stone Cold Steve Austin announced Lawler had won the match but the Anonymous Raw General Manager reversed the decision, due to Austin getting involved in the match. A month later at Extreme Rules, Cole teamed with Swagger to defeat Jim Ross and Lawler in a Country Whipping match. Lawler and Cole had a final "Kiss My Foot" match at Over The Limit on May 22, during which Bret Hart returned and put Cole in his signature submission move, the Sharpshooter, to help Lawler make Cole kiss his foot. Cole apologized to Lawler the following night on Raw, ending their feud. Cole continued to favor most villains and question the actions of the fan favorites to regain control in matches.
Cole continued to wrestle sporadically after this. On the July 25 episode of Raw, Triple H placed Cole in a match against Zack Ryder, which Cole lost quickly. Cole and Alberto Del Rio lost a tag team match to John Cena and Jim Ross on October 17. This prompted Cole to challenge Ross to the "Michael Cole Challenge" (a series of three contests); Cole said that if Ross won each challenge, Cole would quit his job. During the challenge on November 14, Ross won the first two challenges (arm wrestling and dancing), causing Cole to declare that the third contest was who weighed less, which Cole won. Ross was subsequently fired and CM Punk came out and attacked Cole; Cole vowed revenge and said he would sue Punk for injuring him. Cole was a surprise entrant in the 2012 Royal Rumble match but was quickly eliminated by Lawler, Booker T, and the returning Kharma. Cole was put in a match with John Cena on the June 4, 2012, episode of Raw, which he lost, and was forced to make an apology for all of his wrongdoings.
On the July 9 episode of Raw, Cole was booked against Jerry Lawler in a WrestleMania XXVII rematch, which he quickly lost. The Anonymous Raw General Manager reversed the decision, making Cole the winner by disqualification following interference by Booker T. Santino Marella then came out and pulled out Hornswoggle from hiding underneath the ring, claiming that he was the Anonymous GM.
Cole was lauded for his handling of his fellow commentary partner Jerry Lawler's legitimate on-air heart attack on the September 10, 2012 episode of Raw. In spite of being a heel commentator for two years, Cole provided updates to television viewers on Lawler's condition throughout the episode and was described as "classy and professional", and praised for his handling of the emergency. The incident effectively turned him face for the first time since 2010, as he began favoring the face wrestlers and began receiving cheers. Cole also joined in commentary during Raw and pay-per-view events, including Night of Champions and Hell in a Cell by Jim Ross and John "Bradshaw" Layfield. Cole cemented his face turn when he hugged Lawler in the ring when Lawler returned on the November 12 episode of Raw.
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 did not appear on commentary the following week as part of a storyline injury. On June 8, Cole welcomed Byron Saxton as the color commentator for Raw, replacing Booker T. On the January 15, 2018 episode of Raw, Cole was attacked by Braun Strowman due to Strowman's anger at being fired by General Manager Kurt Angle, and was subsequently replaced by Tom Phillips for the remainder of the broadcast. On September 26, 2019, WWE announced as a part of their "WWE Premiere Week" that a new commentary team would be on SmackDown. Cole would return to commentary on SmackDown for the first time since he was drafted to Raw in over eleven years, alongside former Raw commentators Corey Graves and special contributor Renee Young. He was joined on commentary by Pat McAfee on April 16, 2021. McAfee would take a break in late 2022, and Cole would be joined by Wade Barrett on commentary.
On August 8, 2023, Cole returned to the Raw announce desk alongside Wade Barrett. He also remained on SmackDown alongside Corey Graves and Kevin Patrick.