Miranda Lambert won four awards, including album and song of the year, but the singer lost the night's top prize to Luke Bryan at Sunday's Academy of Country Music Awards.
It was a repeat of the Country Music Association Awards in November, where Lambert won multiple prizes but lost the big award to Bryan.
"Listen guys, what an amazing night of music," an excited Bryan said onstage after winning the fan-voted award. "Thank you to my wife, my kids ... my fans, country radio."
Lambert was the sole female nominated for entertainer of the year; other nominees included Garth Brooks, Jason Aldean and Florida Georgia Line, who won two awards Sunday at the AT&T Stadium.
Though she lost the top prize — again — Lambert was the queen of the night. She was on a red-hot winning streak — and she even rocked a red-hot bustier when she performed "Little Red Wagon."
Lambert won her fourth album of the year, her sixth female vocalist of the year and her third single record of the year (she won twice this year as a performer and songwriter of "Automatic.")
"I don't even realize what's happening tonight," Lambert said. "I love my job so much. I will never not love my job."
Lambert, a fashion favorite in the last year, wowed again in a flowing, plunging dress on the red carpet. Inside the venue, she wore white pants and a white top with a black sheer center. She also accepted the 50th Anniversary Milestone Award, given to her by Reese Witherspoon and Sofia Vergara (Lambert wrote a song for their new film, "Hot Pursuit.")
It was also a memorable night for Taylor Swift, who made it a family affair.
The singer was one of seven recipients of the Milestone Award, and a video package highlighting her career and success played before her mother, who recently announced she is battling cancer, presented her daughter with the award.
"I am a very proud mom," said Andrea Swift, who also called her daughter "brave enough to explore her musical curiosity."
"I am so happy I learned how to write songs in a town like Nashville," said Swift, who released her first full-blown pop album, "1989," last year.
The former country singer, who sat next to her father Scott Swift, danced along in typical form, especially when Lambert and Martina McBride performed.
Other recipients of the anniversary honor include Brooks, Reba McEntire, Brooks & Dunn, Kenny Chesney and George Strait, who performed near the beginning of the show.
The ACMs kicked off paying tribute to veteran Merle Haggard by Keith Urban and Eric Church, while Strait sang "All My Ex's Live in Texas" — appropriate for the awards show celebrating its 50th anniversary in a new location, the Dallas Cowboys Stadium in Arlington, Texas.
Shelton and Bryan were playful as hosts — and they even played some football. Shelton asked Cowboys quarterback Tony Romo to throw the ball to Bryan, who was wearing gloves.
"This isn't one of those deflated balls?" Shelton said after Bryan caught the ball, referencing the deflategate scandal earlier this year.
Shelton announced that the — usually held in Las Vegas — set a Guinness World Record for most attended live awards show of all-time.
Shelton and Bryan performed, too. Christina Aguilera joined Rascal Flatts and Nick Jonas sang with the country duo Dan + Shay.
Brooks' performance of "All American Kind" marked a sentimental moment since it included U.S soldiers standing proudly.
"I'd like ... to thank all of our men and women in the armed forces ... protecting our freedom," Brooks said when he received the Milestone Award from Taya Kyle, the wife of the late "American Sniper" Chris Kyle.
Lee Brice sang some of "Forever and Ever, Amen" and then called out Randy Travis, who was sitting in the audience and earned a rousing applause. Brice won single record of the year for "I Don't Dance," which he also produced.
"This is insane. Thank y'all so much," he said.
Little Big Town had one of the night's top performances when they slowed things down with their recent hit, the semi-controversial "Girl Crush." They won vocal group of the year, and Cole Swindell won new artist of the year.
Dierks Bentley, who had seven nominations, won video of the year for "Drunk on a Plane"; Aldean won male vocalist of the year.
Other performers included Brooks & Dunn, Brad Paisley and Alan Jackson.