The Egyptian striker joined Tottenham on an 18-month loan deal in January 2005 and signed permanently when it had run its course.
But that was only after turning his back on Raiola, who told Mido not to sign until the last week of the transfer window.
Mido held talks with Spurs chairman Daniel Levy and put pen to paper on a contract – only for Real Madrid to make enquiries over signing him.
It was Mido’s ‘dream’ to join the Bernabeu giants but he had already committed to Spurs and they instead moved for Antonio Cassano.
“Sometimes now I look back at my career and I’m like I wish I listened more to Mino,” Mido told the Tranfer Talk podcast.
“Mino was giving me a lot of advice I didn’t listen to. I didn’t. Sometimes I paid for it. For example, when I came to Tottenham I came on an 18-month loan at the beginning and I went back to Roma.
“Luciano Spalletti was the manager and Mino said to me ‘Mido, you have to wait until the last week of the transfer period’.
“I was like ‘no, I want to go back to Tottenham’. Daniel Levy was on the phone to me and Martin Jol was on the phone and then I remember Berbatov in the first two or three games didn’t play well.”
“Martin Jol panicked and was like ‘you have to come back, you have to come back’ so after the Super game against Inter I said ‘I want to go tomorrow to Tottenham, you finish this deal’.
“Anyway, Daniel Levy came to Roma on easyJet. It’s true! We signed the deal and he was like ‘Mido, come on, run, run, run’ – I thought it came with a private jet.
“He said ‘no, to get a good seat’. But that’s Daniel Levy, it’s the key to his success isn’t it?
“When we arrived to Stansted airport, Mino was like ‘don’t sign, don’t sign’. I nearly signed behind Mino’s back, actually.”
“We landed at Stansted and Fabio Capello was the manager of Real Madrid and his assistant was Franco Baldini. When I landed there I had four or five missed calls from Mino when I was on the plane.
“I landed and called Mino and he said ‘I told you not to sign’. I said ‘why?’ and he said ‘Real Madrid want you, they want to swap you with Julio Baptista’.
“I said ‘I’ve just signed for Tottenham’ so he said ‘pass the phone to Daniel Levy’.
“He took the phone and Daniel Levy was like ‘aha, he was laughing, and he said ‘no problem, he’s not going anywhere’.”
Mido went on to have an unsuccessful season where he slipped down the pecking order before being sold to Middlesbrough.
“It was one of my dreams to play for Real Madrid. Real Madrid ended up swapping Baptista for Cassano,” Mido added.
“It was one of my dreams but in football everything could happen. One of the things I regret is that I didn’t listen enough to Mino.
“Mino always told me the difference between you and Zlatan Ibrahimovic, because we were both with Mino since we were young, if I tell you both to build a sand castle, you will do it. If I tell you both to break it, Zlatan would do it and you will not. You will tell me ‘no, why would I do that I just built it?’
“Sometimes I think it’s good in football to be a little bit daft. It’s good not to think a lot, to worry about the future and that’s the case.”