Siddle and Gardner Webb's victory over Kentucky was the school's first over a ranked team. UNC Wilmington's road win over Kentucky secured its first over a ranked team.
Before Saturday's matchup, Siddle told ESPN he didn't dwell on the feat at Rupp Arena as a player when he talked to his team. But he did use it as motivation.
"One thing I told the guys about when we pulled it off [in 2007] is that it's going to be really loud in there and, as we continue to respond, it's going to get really quiet in there and everyone is going to start leaving early and that's what happened," Siddle said after the win. "That's when I had a déjà vu moment."
The 2007 Wildcats, coached by Billy Gillispie, hadn't lost a regular-season game to a mid-major program in six years before they fell to Gardner Webb. On Saturday, Siddle's squad was an 18.5-point underdog, according to ESPN BET.
Kentucky's loss capped a weekend filled with upsets among Top 25 teams. On Saturday, No. 3 Marquette lost 75-64 at Wisconsin and No. 7 Duke suffered a 72-68 defeat at Georgia Tech. Also, No. 18 Villanova lost its third Big 5 game of the season in a 57-55 loss to Drexel at home.
According to ESPN Stats & Information, Saturday was the first time in The Associated Press poll era that Duke, Kentucky and Villanova all lost to unranked opponents on the same day when they were all ranked.
Kentucky's setback extended a wild 24 hours in college basketball. On Friday, Northwestern beat No. 1 Purdue 92-88 in overtime and No. 4 UConn suffered a 69-65 loss at No. 5 Kansas. With its 82-55 win over Colgate on Saturday, No. 2 Arizona will likely be the No. 1 team when the AP Top 25 is released Monday.
But UNC Wilmington's victory stood out amid the chaos.
On Thursday, UNC Wilmington lost at East Carolina 74-66. Siddle said the loss humbled his team and helped it prepare for Saturday's game.
John Calipari's squad lost control early. UNC Wilmington had a 38-24 edge after Nolan Hodge hit a 3-pointer with 2:55 to play in the first half.
Five minutes into the second half, however, Kentucky took the lead, but Shykeim Phillips (13 points, 6 rebounds, 4 assists) made clutch plays and Trazarien White (27 points, 10 rebounds) kept scoring to help seal the win down the stretch for UNC Wilmington. Kentucky's Reed Sheppard led his team with 25 points.
Siddle said White and Phillips helped his squad maintain its composure as Kentucky fought back in the second half.
"I thought our upperclassmen, Phillips and White, they've been in big moments with me a lot," Siddle said. "I thought they did a really good job calming everybody down and making sure we executed as a group."
After the game, Siddle said he reflected on the moment he achieved as a player while he celebrated as a coach. He said his team remembered his pregame message about the possibility of an upset.
"They don't want to hear about my glory days," he said. "It was so long ago. My main message was 'It can happen, but you just gotta believe it can happen.'"