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The side went down 2-1 to Auckland side Bay Olympic in an even contest in which chances came, but defence dominated for long periods of the game.
The Auckland side scored two goals near the end of the first half when Caversham were down to 10 men.
Midfielder Ben Wade picked up a cut to the head and when he was off, Bay Olympic scored a couple of goals.
Bay Olympic coach Paul Marshall felt that was a key part of the match which tipped it in favour of his team.
"It was pretty even I thought, but when they had that injury that enabled us to score those two goals and in the end that was the difference," he said.
"It was even right throughout - they had some chances and so did we. It's a cup tie so to dominate right throughout is probably not realistic."
It was Bay Olympic's deepest run in the cup for more than 50 years. The side plays in the North first division after being relegated from the Northern Premier Division last season, so it was a good boost for the side to get the chance to get into the semifinals of the cup.
The side had a game tomorrow in the league as it fights to get back into the top division.
The Auckland side went ahead just past the half hour mark.
The ball went to the left, and left back Jonathan Quinn did a nice one-two and managed to hold off the defenders to put the ball past Caversham goalkeeper Liam Little.
Five minutes later, and it was 2-0. A high ball swung into the penalty box, and Little went up to get the ball, but in a contested challenge it bounced free. Bay Olympic striker Jared Colligan was first to the ball and he scuffed it into the net.
Bay Olympic went into the break with plenty of confidence and into the second half, sat back and let Caversham have the ball. The visiting side closed down the space in its back third and there were few holes.
Half an hour into the second half, a Caversham free kick floated into the penalty area and referee Dan Woulahan found a penalty, saying Colligan pushed a player in the penalty box. Most of the crowd seemed puzzled, but Connor Neil calmly stepped up and nailed the spot kick, hammering the ball into the bottom right hand corner.
The game opened up more as Caversham hunted for the goal which would tie up the match, but it would not come.
In the extra minutes - which Marshall felt were twice as long as they should have been - Caversham threw nearly everyone forward but never really got close.
Caversham coach Richard Murray was not disappointed with the performance of his team, and said the match was very even.
He had no qualms with having Wade off the field for more than five minutes when Bay Olympic scored its goals.
"We were really in the game in that second half. They sat back and let us come to them but we couldn't get through. The guys tried hard but they are a class team with some guys who controlled the ball well," Murray said.
Best for Caversham was captain Andrew Ridden and Wade, while substitute Campbell Thompson made some lively runs on the left when he came on in the second half.