Now working for TNT Sports, talkSPORT alumni Woods has been given the job of main presenter after BT Sport rebranded and has had the chance to speak to the biggest players in the Premier League.
And that includes Maddison, who left Leicester this summer after they were relegated to the Championship.
He signed for Tottenham as one of Ange Postecoglou's new arrivals for around £40million.
All in all, the deal has been commended as the right kind of purchase Spurs were desperate for - a creative-minded attacking midfielder, who can bring some excitement back to the north London club.
But not all are in agreement it appears after Woods, a massive Arsenal fan, poked a bit of fun at the England international over his transfer.
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Speaking with TNT Sports in a pub alongside Ally McCoist, Woods said: "Another thing me and Ally share is a real joy of watching you play football.
"It is not just football, we love your interviews and your personality in general, which begs the question… why Spurs?"
It led the trio to break out into laughter while Maddison looked stunned and pointed the finger and said: "Arsenal fan, Laura, in case you didn't know!"
Woods replied: "I am only jealous because I wanted you to come to us!"
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After some giggles were shared, Maddison gave his serious answer saying: "My time at Leicester did not finish how I wanted it to.
"We obviously went down in the end which was very disappointing, very sad.
"So I wanted to end it on a good note but it wasn't to be.
"You get to those parts in life where you get set back and this was the next step for me.
"People have asked 'why Spurs?' and whatnot but you have to make a decision, not just at work but in your life.
"I could see myself playing for Spurs, as a Tottenham player, as much as that might annoy you, Laura!"
Maddison is currently a doubt for Tottenham's clash against Bournemouth this weekend after suffering a foot injury.
When the 26-year-old will return remains to be seen but the problem is not a serious one and he could be fit for the Carabao Cup clash against Fulham on Tuesday.