James Maddison cheekily claimed Simon Jordan doesn't understand how to make a successful football team with the pair trading verbal blows of late.
Spurs' Europa League final victory over Manchester United saw Maddison pick up a winner’s medal despite missing the game through injury.
He contributed three goals and four assists to his side’s triumphant European campaign.
In the aftermath of last week’s celebrations in Bilbao, Maddison posted a clip of Jordan critiquing Maddison’s trophy-winning credentials during a talkSPORT broadcast in February.
In response, Madddison captioned the clip of him holding the trophy: "Bookmarked it. Knew it would come in handy.”
Maddison uploaded a clip of talkSPORT pundit and former Crystal Palace owner Jordan questioning his trophy-winning credentials.
"If you want to win something, you've got to bring players in that are able to operate at the highest level," he said in February.
The ex-Crystal Palace owner was in no mood to give Maddison the final word.
“It’s good he listens to the show after his performance… oh he didn’t play in the game did he?,” Jordan said on Tuesday.
The talkSPORT pundit then dug a little deeper and took aim at Maddison’s role in Leicester’s dismal relegation campaign of 2022/23.
“The ultimate Maddison effect is you win things now with James Maddison and your team gets relegated,” he added.
And Jordan didn’t stop there.
“Perhaps if he’d been available for Spurs more this season they might have got relegated. They did their very best to try to didn’t they by finishing fourth from bottom?" Jordan continued.
“But he’s right, if people make an observation they should be held accountable for it."
Once Jordan had disposed of his pops at the England international, he did concede that Maddison was in his right to hit back before questioning whether it was the right action in the context of the handbags.
“If a team or individual achieves something there’s a balancing act between having the strength of character to say to somebody ‘you’re irrelevant so I don’t care about your opinion or empowering that person by saying I do value your opinion and you were wrong,’ Jordan added.
“I don’t mind either way. He pulled up Roy [Keane] about it as well didn’t he?”
Maddison previously came under fire from Keane who suggested he was lacking in consistency, before Maddison later responded by scoring against United.
Following last week's final, Maddison responded in an interview with CBS Sports for whom Keane was providing punditry analysis.
"I wasn't gonna do any interviews but I heard Roy Keane was in the studio tonight," the Spurs star said.
Studio guest Micah Richards then urged him to throw the imaginary darts, to which he agreed, adding: "Oh I will, Micah, with pleasure!"
That led to Keane replying: "I always said he was a good player but he needs to be more consistent. And he played well tonight!"
With Maddison at the centre of tiffs with two of football's most prominent voices, there was only one way to address the situation.
As is often the case on the world's biggest radio station, talkSPORT were quick in obtaining a reply from Maddison to Jordan's latest blast.
The Tottenham playmaker joined talkSPORT Drive later on Tuesday and appeared to pour cold water on any possible conflict, but maybe included a couple of cheeky digs for good measure.
"I don’t want to get into a pillow fight with Simon Jordan but even with the Roy Keane thing, it’s all a bit tongue-in-cheek," Maddison said.
"Over the course of a season as a player, you have accept people in the media giving you criticism. That’s part and parcel.
"But when you win the trophy as a club, if you’re not entitled to have a dig back, then what's the point?"
He continued: "People always want personality. They moan there’s not enough personality in players and they are all robots with the same generic answers.
"Then as soon as we show a bit of personality, we get shot down for that too. But I'll never change.
"It just tells me that Simon Jordan doesn’t quite understand what it takes to be a successful team.
"It’s not just about the 11 players who play. It’s not just about the players. It’s about the team behind the team. We all win together."
Maddison continued: "It's a long season, especially with the new format with the extra games and it takes everything.
"It takes all the squad all players used all staff involved to get us the players in the right place to be able to go and win and we did that and we're so happy.
"So we win as a collective so everyone involved wins the Tottenham fans when we all win, Sir Simon wants to try to take that away from me then be my guest.
"But maybe just eat a bit humble pie put your hands up and say, 'okay, maybe James Madison did win this season'".
The Tottenham star will now put his energy into recovering from a knee injury sustained in the Europa League semi-final first-leg win over Bodo/Glimt.
There were fears Maddison could miss the beginning of next season but it now appears that the 28-year-old will overcome his injury woes in time for the August restart.