A place in the Scottish Cup semi final in up for grabs on Tuesday night as the ex-Hibs and Celtic defender hopes to exert some pain on Hearts.
Caldwell’s last appearance at the ground as a player saw him red carded after 31 minutes in a 2-1 defeat to the Gorgie side in December 2009.
He has also had to endure physical pain but still retains a fondness for the stadium.
Caldwell said: “In different matches there I’ve broken my ribs, punctured my lung and been sent off, so it’s not a place I have great memories of!
“I always looked forward to going there, though, because of the atmosphere. Because I played for Hibs and Celtic, these were always big games and their support has always been very vocal.
“They do get behind their team and it is important that we are ready for it. They are a physical side, but they were a physical team even when I played against them.”
Despite recent incidents with fans entering the pitch, north and south of the border, Caldwell has no such worries about the same thing happening at Tynecastle.
However, he does expect plenty of stick from the home support.
“I don’t think there’ll be any issue regarding the support being close to the technical areas,” he said.
“We hope the fans come to support their teams and there can be a bit of banter. But once it crosses the line and becomes physical, that’s when it’s wrong.
“It’s not just in Scotland. What happened at Birmingham on Sunday was ridiculous. We have to get it out there that this isn’t just a Scottish thing. Yes, we have elements up here that we’re not happy with and we need to change for the good of our game.
He added: “I’d fully expect the Hearts fans to have their chants and they can sing songs about me, although I’d like to point out that my assistant Brian Kerr played for Hibs as well, so they can send some towards him too!”
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