"It's a headache I haven't had for many years ... maybe ever," he says as his troops continue on a successful campaign despite losing 2-1 to Team Wellington at Bluewater Stadium, Napier, on December 1.
Their fifth placing on the premiership table is an aberration after they forfeited three points last Sunday for fielding new signing Harry Edge as a substitute in their 3-1 victory over newcomers Wanderers Soccer Club in Auckland when the paperwork wasn't rubberstamped to transfer the former Waikato United midfielder.
"It came as a big shock to us," says Greatholder who had savoured a return to a shared top-of-the-table existence with leaders Auckland City.
However, the Bay boys have taken losing the game on paper in their stride and will instead vent their frustration on a resurgent Southern United tonight.
"We'll be using the loss of points as extra motivation."
Greatholder says he had his eye on Edge, the son of former All Whites international striker Declan Edge and ex-coach of the defunct Waikato United, during the Central League winter season when the youngster was playing for Western Suburbs in Wellington.
"He's a young lad and he was carrying one or two injuries so that's why we didn't sign him up straight away."
Edge will go down to the franchise youth squad this weekend to regain premiership match fitness.
Nevertheless, Greatholder isn't under any illusions that the hosts are a much-improved outfit under Brazilian coach Luiz Uehara after losing 3-2 to Bay United in Napier after leading 2-1 at halftime.
The Southerners had also lost 3-0 in their opening-round encounter to Waitakere United but last weekend showed immense character to whip the Aucklanders 3-1 at Kiwitea St.
Like Wellington Phoenix coach Ernie Merrick, Uehara had impressed it was taking time and patience to instil in his youthful squad the need to embrace a passing game.
Says Greatholder: "Southern United are a very good side. They are very well organised and disciplined. They'll be pumped up so it'll be tough for us."
Robertson returns after serving a match suspension last week for collecting two yellow cards in their away 4-4 draw against Auckland City.
No doubt reshuffling the Beefeaters won't be as challenging for Greatholder as it must be to reorganise the engine room and coal face although he takes a good 10-15 minutes to explain to players who fail to make the cut why they didn't cut the mustard.
"We now have two players fighting for just about every position."
No one knows that better than Dunedin-born Harley Rodeka who warmed the bench last weekend but didn't run on because of a tummy bug.
The 25-year-old started the season as a winger but eventually found himself in defence.
"Obviously every player wants to be out there playing rather than sitting on the bench."
It took him a while to adjust to the demands of playing rightback, finding it difficult to roam up the flanks with that nagging reminder that he is their primarily to fall back in the blink of an eye.
"To be honest, though, it wasn't too bad," says the utility player who will be hoping to make an impression off the bench today with family and friends watching.
"I don't mind playing there but I think I did a good job although I had to learn a lot because I have no experience in defending."
Rodeka is among players who have knocked on Greatholder's door to try to figure out why they are on the fringe of making the starting XI.
He won't venture into the details on what transpired except to say he has taken on board feedback from the coach and is working on it.
He reiterates Greatholder's sentiments that training nights on Tuesdays, Thursdays and Fridays resemble almost match intensity as players jostle to earn their stripes.
So what will Rodeka do regain his berth? He suspects players tend to go through phases in a season - those who start with a hiss and a roar but fizzle after a few rounds and those who start slowly but peak after a few games under their belt.
So where exactly does Rodeka sit in the scheme of things?
"I'm not too sure, mate. That's a good question. I don't have the answer right now. I'll have to think about that one.
"No matter what sport you play ... it's something you have to deal with."