The Bill Robertson-skippered Bay United face Canterbury United at ASB Football Park, Christchurch, in a 2pm kick-off tomorrow.
Three Bay United players - centreback Robertson, midfielder Conor Tinnion and striker Sean Lovemore - were also named in the team of the month.
Those endorsements come on the heels of a concerted campaign to clinch a maiden play-off berth in the nine-year history of the premiership.
That Bay United sit on the second rung of the premiership table, on equal 10 points with leaders Waitakere United but inferior on goal difference after three wins and a draw each, is a testimony to how determined the Bay are in breaking that hoodoo.
While delighted with the latest offerings, Greatholder doesn't want to lose sight of the bigger picture. "We're trying not to get too carried away with it."
He finds comfort in the cliche of merely starting a journey.
Breaking it down to the lowest common denominator, the Englishman believes the franchise is reaping the benefits of investing time, money and effort into a youth team structure and culture that are paying dividends, albeit incrementally.
Admittedly, the father of three feels helpless at times on the sideline on match days.
"You put your trust in the boys to do the job, I suppose."
One of the lads in the playing squad as early as last summer, Greatholder found himself assuming the mantle of coaching when coach Matt Chandler announced three matches into last season he was leaving to work in Australia.
Needless to say, it would have taken the hardiest of souls to want to turn around the misfortunes of a team who frustratingly lost games other teams would bracket as must-wins at the start of a season.
Against such insurmountable odds and critical media reviews, Greatholder often found himself re-evaluating his future, but through such self-assessments the willingness to prove detractors wrong fuelled his desire to flag the easy way out.
Trying to milk the best out of individuals and stimulate them to think on their feet form the basis of fulfilling that desire.
He feels his managerial position at the TSB Bank in Napier, in motivating teams of five to 18 staff, has enabled him to employ those tactics to rejuvenate players on the park.
"I really enjoy seeing people develop and progress so that's how I get my kicks."
No doubt, he reveals Bay United players are elite athletes who are more highly strung and, thus, motivated to succeed.
That appraisal, however, comes with a sobering realisation that coaching is merely a hobby for a man who has a full-time job to provide for his family.
Juggling time between his job and anywhere from 20 to at least 25 hours a week on the field behind Bluewater Stadium, Park Island, is demanding enough.
The residual time from that is preciously spent with "lovely wife Kate" and their children, Ruby, 8, Molly, 6, and Harry, 3, who more often than not are in bed when he pulls up the driveway to their Havelock North home.
"She [Kate] knows how much it means to me. We do it together and it needs to be like that," Greatholder says of his wife, who is always at home matches with the kids.
That hobby requires Monday night video and statistical analysis on how the game panned out and what to tweak, even after victories.
He hastens to add the input from Cotton and the other backroom staff is undeniably pivotal in "perfecting the craft" that also yielded a 1-1 draw with O-League campaigners Auckland City at Kiwitea St.
His troops at the coalface share the kudos, too.
"The funny thing is when I was first told three players were named in the team of the month I could have taken a guess but I wasn't exactly sure who they could have been," he says, feeling defenders Aaron Jones, Fergus Neil and English import striker Stephen Hoyle could have easily made that team.
"We have to educate the boys about the game as well."
Tomorrow, anticipation will give way at the artificial turf in Christchurch when they arrive about two hours before kick-off to come to grips with the surface.
The memory of George Slefendorfas netting five goals in the 7-0 routing there on a "freakish day" is still fresh.
Third-placed Canterbury lost their opening match to Auckland City, who are in fourth place with two draws.
The last time the Bay were victors over the Dragons in Christchurch was in 2009 when they thrashed the hosts 4-0.
In this month's awards, Canterbury's Russell Kamo was named player of the month, pipping golden boot Sean Lovemore.
Coming to terms with the artificial surface is paramount in Greatholder's books.
"Sometimes, the ball holds up and the second bounce is as true as the first one."
Former Otago United winger Harley Rodeka returns from a one-match suspension after collecting a red card against Auckland and sitting out last Sunday's 2-0 victory over his former home club in Napier.
Luke Chapman makes way for Rodeka, while strikers Jarrod Smith and Dakota Lucas are still recovering.
"They could be on the bench in the away match against Waitakere United," Greatholder says of the match at Fred Taylor Park the following Sunday.
"Both of them are classy players, so we'll try to add them to our roster for exciting times ahead."
Savouring the winning streak so far without several key players, Greatholder says their return will create a selection headache but one he'll relish as the race towards making a historic play-off beckons.