The Manchester United technical director is set to put rivalry aside when Josh and Tyler, who turn 16 this season, put pen to paper on professional contracts.
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Fletcher spent more than two decades at Old Trafford and made 342 appearances for the club, but he is not the only Red Devils legend to use the City Football Academy.
Wayne Rooney, Robin van Persie, Phil Neville, Andrew Cole and Viv Anderson have all sent their kids to the blue side of Manchester in recent years.
However, for West Ham legend Carlton Cole, there is a line that cannot be crossed.
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The former England striker, who spent nine years with the Hammers, insists his son could not play for arch-rivals Millwall.
After Liverpool fan Adebayo Akinfenwa admitted he would be happy for his kids to play for Merseyside neighbours Everton, Cole said he felt differently.
"You have to have a moral compass," he told talkSPORT. "I'm West Ham and a bit of Chelsea.
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"I can't see my son playing for Tottenham or Millwall. It's a no-go zone."
Explaining his point, Cole joked that the logistics simply would not work.
He added: "I wouldn't be able to support them. If he went to Millwall, I wouldn't be able to go down there!
"I would get pelters. I would have to go in disguise.
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"I would love my son to just make it in general, to live his dream, but if it's the wrong club… you do think about it!
"If I went, I'd have to go with some armoury. I'm scared for my life over there, you've not seen the way they've treated me!"