The club has exited at the semifinal stage three times in that same period, including 2009, but did successfully navigate an away semifinal in 2004 on its way to the title. The Wellingtonians last won the Cup in 2010.
"I'm pretty excited," Raccuglia said. "This is my first semi final since I came to this country and we'll try our best to win this game. I've done my homework, I think, and I know the history of Central United and their links with Auckland City. It's a club celebrating their 50th Jubilee but hopefully we can do something to stop that."
Raccuglia arrived in New Zealand just eight months ago but said taking over from former coach Matt Calcott had been a seamless transition for him.
Both Central United and Miramar Rangers have won the Chatham Cup four times each.
Meanwhile, Caversham have never made it to the final of the 88-year-old knockout competition - this year is just the seventh time they have made the last four following a heart-breaking 2-1 defeat to Napier City Rovers at the same stage last year.
However, Caversham coach Richard Murray said that experience may be lost to his side with only six players returning to the club this season and has mixed feelings on the subject.
"We have such a high turnover of players here with students coming and going but in saying that this presents new opportunities for other players and it could be just another game for them," Murray said.
Caversham will be without two key players. Striker Tom Jackson has returned to the USA, while Otago United marksman, Ant Hancock, is an injury doubt, but Murray hopes local support can make a difference.
"Now we're at home in the semis everyone here, even from other clubs - particularly the older club life members - have extended their well wishes. Going on a good Cup run means local people want to come and see good football," he said.
Caversham eased through the early rounds with some narrow victories - including a nervy 3-2 win over Roslyn Wakari in the fourth round - before disposing of Manukau City 3-1 in the quarter-finals.
Chatham Cup Semi-finals
At Caledonian, Dunedin: Caversham v Lower Hutt City, Sunday, Kick-off: 1pm
At David Farrington Park, Wellington: Miramar Rangers v Central United, Sunday, Kick-off: 2pm