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The world No.49 probably could not imagine that he would end up beating the same subject in the last 64, especially as he had been stuffed 4-0 in their last encounter.
Grace – who hit a top break of 94 – came from 2-0 down to win 4-3 but overcame nervy moments in the penultimate frame when he could have thrown it all away.
Grace, who now faces China’s Tian Pengfei, said: “I made hard work of that. I got over the line in the end.
“You don’t normally get a second chance against Ronnie. I could have won 4-2 but lost cue ball and missed a smelly one.
“That’s when the snooker Gods don’t forgive you but luckily they were on my side today.
“At 2-0 down, it was going really badly and I am proud I found the cue-ball control to get a foothold in the match.
“When you play the legends, they get better when they go in front.
“I have wanted to prove I can do it on the biggest stage – anyone down the rankings does that – and when you have a chance you have to take it.”
On his passion and hobby for the canvas, Grace added: “I’ve done a few paintings in the past. I have had to give it a backseat as I don’t have the time when I play snooker matches.
“I’ve done one of Ronnie, which I did last summer for a fella.”
O’Sullivan’s last Home Nations Series win came five years ago in the English Open and he follows top rival Judd Trump out of the early exit door this week in Belfast.
Jimmy White, the six-time world championship finalist, said: “David Grace played fantastically well and showed what a great player he is.
“To do it on the centre stage against the world champion in a venue like this – it will be great confidence for him going forward. He deserved his win despite being 2-0 down.”