Leeds-born Montgomery admits he would love nothing more than to face the Whites in the Premiership next season.
And he believes it is a serious prospect after being impressed by Leeds during Tuesday night's 1-1 draw at Bramall Lane.
Montgomery, who was released at Leeds as a youngster, said: "After that performance, I think Leeds showed they have got what it takes to go up.
"We went out there under no pressure and I thought we played a lot of good football, but they held us back and I think they'll be a good punt in the play-offs.
"I wish them all the best because I've been a Leeds supporter since I was a young boy.
"But I'm a Blade now because I've been here since I left school and this is where it all began for me."