More than 20 years may have elapsed since a grim August night for Rangers back in 1986 but the manager still shudders at the memory.

Smith had just arrived at Ibrox as assistant to new boss Graeme Souness and both men watched in despair as Rangers failed to find the back of the net during regulation time.

They finally sealed their progression to the fourth round of the League Cup after a nerve-shredding penalty shoot-out.

When the teams meet again in the third round of the CIS Insurance Cup tomorrow, Smith claims the threat from the Fifers will be no less serious.

And he has made sure the class of 2007 are under no illusions as to how easily it can all go wrong on the night if they are not properly focused.

"It was a typical cup tie and I remember we had to score five penalties to go through," he recalled. "We won 5-4 on penalties and Ian Durrant scored the last one much to our relief. I mentioned that game this morning to everyone.

"We were in a similar situation as we are now, in that we were a new team, with new players still getting together. It was a tough night, it was a hard night for everyone. Hopefully we can avoid that again!"

East Fife sit top of the Third Division and have already claimed one SPL scalp in the shape of St Mirren in the last round.

As if that was not incentive enough, chairman Willie Gray has offered his players a holiday in Barbados if they can pull off another shock at East End Park tomorrow night.

Smith said: "East Fife beat St Mirren in the last round so it will be extremely competitive, that's what you get in all the Scottish cup competitions.

"You are never comfortable in these games, your team has to compete fully.

"It's a huge game for East Fife, everyone at Rangers knows that, and we will have to match their levels of determination if we hope to progress. If we don't do that, we will be in trouble.

"They have already knocked out one Premier League club so they have shown they have a quality of play to step up and beat opposition from a higher league. We go into the game with that awareness."

The CIS Insurance Cup represents Smith's first chance to win silverware since his return to the Ibrox helm, and he added: "It's a trophy we want to be involved in right to the end.

"Everyone will need to be fully committed tomorrow night if we are going to win through."

Mass changes will be made to the side which defeated Aberdeen in the Clydesdale Bank Premier League at the weekend.

Long-term injury casualties Ugo Ehiogu and Thomas Buffel will be involved for the first time this season while goalkeeper Roy Carroll and Alan Gow are set to make their competitive bows.

Other fringe players, such as Kirk Broadfoot, Chris Burke and Charlie Adam, are also likely to have a part to play in the third round tie.

"The players who play tomorrow night don't have to prove anything to anybody, they are good players," said Smith. "We will put them out wanting to win the game and to progress in the competition.

"Because of the number of matches we have, I feel we have to keep everyone ready to play and keep a freshness in the rest of the squad."

He added: "We have had quite a number who haven't been involved and who have expressed their disappointment at not being involved but their attitude has been terrific. They train hard and they are keeping themselves ready.

"It's only fair that I give a number of them the opportunity to be involved tomorrow night.

"I wouldn't really want them here if they weren't disappointed but that's part and parcel of coming to any club. We know that we need the numbers to get through the season."