"We have a tie. This has got to be a first!" Urban said, stunned. "I have never heard of it."
The first winner to take the stage was Thomas Rhett, who was overjoyed and pleasantly baffled by the development. "Oh my goodness gracious. Keith, what is happening right now?" Rhett said, smiling, before adorably thanking his wife, his cute kids and all his fans.
Next up was the award's co-winner, Carrie Underwood, whose name is now going down in the history books! With this victory, the 37-year-old singer is the first woman to win the Academy of Country Music Award for Entertainer of the Year three times!
However, she couldn't help but get in a joke about the unusual tie, quipping, "2020, man," as she accepted the trophy.
"I am more than happy to share this with Thomas Rhett and just to have my name mentioned with his... I am beyond honored," Underwood said. "Thank you to everybody here putting on the ACMs tonight. You guys made us all feel safe and you worked so hard and I'm just really glad that we got to celebrate."
Underwood previously won Entertainer of the Year award in 2008 and 2009. Taylor Swift, with wins in 2010 and 2011, is the only other woman who's won the award multiple times. Garth Brooks holds the record for most Entertainer of the Year wins overall, with six total.
After opening the show with an epic medley performance alongside Luke Bryan, Eric Church, Luke Combs and Rhett, Underwood was also tasked with delivering a powerful tribute to trailblazing female Opry members by performing a medley of songs by Patsy Cline, Loretta Lynn, Barbara Mandrell, Martina McBride, Reba McEntire and Dolly Parton.
Watch the video below for more on Underwood.