Bates played with both Middleton and Gilmour at the younger age groups when breaking through at Ibrox.
The trio were all highly regarded at Rangers, but it is now only Middleton who remains with Steven Gerrard’s side.
And Bates believes that both Middleton and Gilmour can go on to have bright futures in the game.
"You’ve got Kieran Tierney, Scott McKenna, John Souttar who could have all played,” Bates said, after Scotland’s under-21 side failed to qualify for the European Championships.
“They’re good players. Boys are getting into the first team. And there’s Billy Gilmour and Glenn Middleton too – the young players here for the next time.”
Bates left Rangers in the summer to make a switch to Hamburg, in what was a controversial move.
Gilmour, meanwhile, opted to leave Rangers for Chelsea and he has gone on to impress in the Premier League side’s development squads.
Middleton has been rewarded for sticking around by Gerrard though, as the young prospect has already received plenty of game time this season, and he is starting to catch the eye.
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