However, defending champions Dale will be mindful they still have to play a Terry O'Neill-coached Promotem Napier City Rovers, who boast current and former Central League squad members and have found some consistency in the past few rounds to park behind the leaders in third place on 28 points.
Their other remaining match is a derby against the Jamie Hall-coached Taradale AFC who are sitting in fourth position with 23 points and, like the Rovers, having played 14 games to the leaders' 13.
Gisborne and Taradale are renowned for playing an expansive game where the wingers are offered a licence to thrill with speed and dexterity as they try to weasel their way around the defenders.
The merits of playing such an exciting brand of football is reflected in the visitors' goal difference of 39 compared with the hosts' 26.
Gisborne have scored 48 goals with Dave Ure humming while Dale have found the net 36 times with former Hawke's Bay United striker Chris McIvor bagging a few hat-tricks.
Just as Penny has kept his house in order, Gissy goalkeeper Mitchell Stuart-Hill is equally adept in keeping rival strikers at berth. Dale have conceded 10 goals to date and Gisborne nine.
"They are by far scoring more goals than us in the league so they're also set up to attack. They won't do anything different."
Taradale also employ a spearhead formation with two men controlling the engine room and their standard four Beefeaters parked in the back.
"We rotate the midfielders and strikers and give two others [on the wings] the licence to roam."
Consequently the pitch conditions will dictate terms and may spoil what has all the ingredients of a humdinger of a match after the sides drew 1-1 at St Childer's Road Reserve in their first round clash with McIvor, Richard Gearey and a few other seniors not playing.
Also, the Gisborne park's sprawling field enables the visitors to use that spread for a yawning attacking formation.
The weather gods haven't been kind, making it difficult for teams to train outdoors. It has also prompted Central Football to shift the game from a soggy Taradale Park to Park Island.
On Thursday, Gilbertson's men worked out at a Napier gym with weights and rowing machines.
"We haven't trained outdoors for the past few weeks. We found out with our older guys that we pick up a lot more injuries indoors."
Gilbertson said with a predominantly ageing but match-savvy squad, the body was crying out for a break considering they were used to training on a friendlier grass surface.
"You're training on grass all season and all of a sudden you're on a harder basketball court and the body just doesn't like it so you don't really want stupid injuries."
Veterans Dean Johnston (ankle injury) and Gearey (calf strain) are the only injury concerns for Dale although the former didn't play last Saturday and looks promising.
The other factor, as Gilbertson points out, is Gisborne are mindful they only have to draw to stay on the top rung and have relatively easier games left to play, including catch-up ones.
Gissy assistant coach Thomas Edge last night said they wouldn't do anything differently because for them it was a bigger game for their younger players.
"The whole idea for us this season was to establish a platform for the young to go on to higher things. If we win, we win. If we don't then we don't," Edge said.
Gisborne, he said, liked to starve the opposition of possession before putting the ball out wide at opportune times.
"We like to give our players a plan to follow but if it doesn't work out then we like to educate them to think for themselves rather than flog a dead horse."
Edge is indebted to the Hawke's Bay clubs and Central Football for letting them field a composite team "when they can be septic about us" playing in the competition.
Gisborne have ruled out promotion to Central League, as have Geon Dale, because of the expense involved in travelling.