The former Red Devils hitman won silverware galore under the iconic Scot
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Wayne Rooney has admitted he regrets the way he handled his transfer request after he tried to leave Manchester United back in 2010.
The Red Devils had missed out on Premier League title glory to Chelsea that year, with the Blues winning the country's ultimate prize under the guidance of Carlo Ancelotti.
The previous year, United had lost both Carlos Tevez and Cristiano Ronaldo - who had been two vital assets for Ferguson at Old Trafford.
Tevez angered fans by choosing to join Manchester City, while Ronaldo was sold to Real Madrid after years of constant speculation.
Wayne Rooney signed a new Manchester United contract back in 2010 after angering Sir Alex Ferguson
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Rooney felt it was the right time to leave United, having grown concerned about the direction the club was heading in.
And the Red Devils icon, speaking on the Stick to Football podcast, has admitted he regrets the way he handled the situation.
Rooney also expressed a belief his relationship with Ferguson was 'never the same', too.
"When I put the transfer request in [to leave Manchester United], I was still speaking to David Gill on where the club was going, how they were going to move forward," he said.
"Being a manager now myself, and looking back, it was the wrong thing to do probably.
"At the time, I felt like it was the right thing to do to really get assurances for my own career.
"Once David [Gill] had explained what the club are doing, I said, 'Fine – that's all the manager had to say. That's all the club had to tell me', and then I signed the new deal.
"In terms of the relationship with the manager [Sir Alex Ferguson], of course it was never the same.
"After that, the big thing that probably hurt him was they had just sold Carlos Tevez, they had just sold Cristiano Ronaldo, and probably couldn't afford to let me go."
Rooney then proceeded to admit he harboured concerns over the signings of Phil Jones and Chris Smalling.
"You could see what was happening and then I started thinking about the team," he added.
"Thinking, 'Right, what's happening with the team?' 'What's going to happen with the manager because we knew he [Sir Alex Ferguson] didn't have that long left.
"The club offered me a new five-year deal but then we just sold [Carlos] Tevez, we just sold [Cristiano] Ronaldo and I said to the manager, 'It's no disrespect to Phil Jones or Chris Smalling – they are obviously not going to replace Ronaldo and Tevez and I just wanted assurances that it wasn't going to be another transition.
"I didn't have the time personally, so I felt it was important to ask the question.
"Is it going to be a three, four-year transition, or is it going to be we're going to win trophies now and he told me to get out of his office – so then I got more sense out of David Gill of what the plan was."
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Wayne Rooney won five Premier League titles while playing under Sir Alex Ferguson at Manchester United
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Gary Neville also spoke on the podcast and admitted he thought there was 'no way back' for Rooney, even if the 38-year-old did go on to sign a new deal.
"I remember being in the dressing room just before a Champions League game when the statement [about Wayne Rooney's transfer request] came out," he recalled.
"I thought that was it – there is no come back from that.
"I'd seen it many times previously over the past 10, 15 years.
"I thought, 'How did that turn around from [Rooney] making that statement?' Me and 'Giggsy' [Ryan Giggs], spoke to [Rooney] the morning after in the gym and said, 'You have to say sorry to the lads', which [he] did.
Wayne Rooney worried for Manchester United after the departures of Cristiano Ronaldo and Carlos Tevez
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"We never thought it would turn around with the manager."
Rooney won two more titles with United after committing his future to the club.
He was a key asset as the Red Devils won the prize in 2011, edging out Chelsea.
But Rooney found himself usurped as Ferguson's talisman by Robin van Persie as United secured title glory in 2013.