A sort of fuzzy logic suggests Ramon Tribulietx-coached City would be preferable although in the chest-thumping arena of the beautiful game showing fear is not etiquette.
Waitakere did, after all, wallop the Bay 3-0 at Bluewater Stadium, Napier, last Sunday although the smart money suggests why strain a muscle to show whose biceps are bigger in what is effectively a dead rubber.
But then Greatholder's face will perhaps emit a hint of consternation, knowing they are uncharacteristically playing today rather than the traditional Sunday.
The Paul Marshall-coached Waitakere will host third-placed Canterbury United at Fred Taylor Park almost 24 hours later.
That does, understandably, rankle with Greatholder a little.
"[Coach] Keith Braithwaite will know what happens on Saturday [today] so if we lose he can rest his key players on Sunday," he laments, wondering why the games aren't played about the same time.
However, he suspects coaches such as Marshall firmly adhere to the philosophy of playing their pivotal players to keep them match fit rather than resting them.
On the flip side, he believes a degree of normalcy will kick in for his troops to catch up with family and friends tomorrow before the playoffs.
On Wednesday, England-born Greatholder relished time on the embankment of McLean Park, Napier, with some of his players watching the ODI between England and the Black Caps.
"It was fantastic because we spent some time bonding."
The Dragons are on 25 points, one ahead of the Bay and boasting a superior goal difference.
In favour of the Bill Robertson-captained Bay will be the absence of five Wellington players, including Bay-born Tom Biss, selected for the Oceania Federation Cup Under-20 Championship in Fiji next month.
Fifth-placed Wellington, who have no hopes of making the semifinals after making the final last season, haven't had much stability in their selections as a feeder club for the Wellington Phoenix franchise.
Greatholder is disappointed with the Bay's efforts last round against Waitakere.
"I don't think we turned up at the park and didn't show much focus from the word go," he said, although happy they had opened them up but not hurt Waitakere.
"We should beat them when we play again with the right sort of mentality."
He hastens to add he asked centreback Robertson and left wing Conor Tinnion not to be confrontational because they are a yellow card away from a two-match suspension.
"They have served a match suspension already so if they pick up another four cards then they'll be out of the playoffs."
That means Robertson will not play today but he's still toying with the idea of taking a risk with Tinnion.
"It's not that I don't trust the players but it whether I can trust the ref. It'll be a borderline call."
Striker Jarrod Smith, who missed a fair chunk of the season due to niggly injuries, is also mothballed for the business end on account of an Achilles tear although the word is he could be out on a painkiller or two if push comes to shove. "He's been working out cardio-wise."
Golden boot contender Sean Lovemore's worst fears were confirmed on Thursday, putting him out for six months. "He's ripped the cartilage off the bone in his ankle. He's really down so it's a shame."