Join us on our own Cup odyssey this year, as we report on cup fortunes in a similar vein. Ahead of round three, we are on the trail with Waitemata FC - an Auckland northern league second division side - after they prevailed over northern premier league heavyweights Central United in the last round. We'll follow their path (or whoever beats them) through to the final on September.
When talking domestic football in New Zealand, Craig Wylie is a man who has been there, done that.
Wylie made his professional debut for the Football Kingz at the age of 17, travelled with the All Whites at 21, played over 300 games in New Zealand's northern league, 100 in the national league and has made two Chatham Cup finals.
But as the final whistle sounded in Waitemata's incredible 2-1 win over Central United in the last round of the Chatham Cup, Wylie achieved a career highlight. He had played a key role in one of the greatest upsets in Chatham Cup history.
Wylie, 32, belongs to the Waitemata old-guard; a group of four close friends - now all in their 30s - who have played at the highest level in New Zealand football and are now past their best. But for the past two seasons they have been comfortably excelling, socialising and having a ball in Auckland's Conference league, and after promotion last year, the Northern League second division.
But no one was expecting the West Auckland minnows to beat five-time Cup winners Central, who were boasting first-choice Auckland City players Emiliano Tade, Angel Berlanga and Marko Dordevic alongside a sprinkling of some of the best young talent in Auckland.
Central took an early 1-0 lead (at which point Waitemata's live in-play odds of winning the game bounced out to 100-1) before hitting the self-destruct button. Central had three players sent off in a frantic final 60 minutes when Waitemata striker Nathan Rollinson scored two great goals to leave the West Auckland faithful rubbing their eyes in disbelief.
"For me, the win was right up there as one of the best moments of my career," said Wylie.
"I've got a strong background with Waitakere so beating Central or Auckland City is always huge, but to do it with this Waitemata team - and the level that we're at compared to where they are - was truly amazing. And to do it at Kiwitea Street was the icing on the cake. I was pretty bloody happy."
Waitemata, coached by former national league player and New Zealand under-20 captain Michael Mayne, have struck a seamless balance of wily experience and youthful exuberance to be sitting on the cusp of two promotions in two years.
Led by exciting English midfielder George Curry and supported by former national league players Colin Gardyne, Joe Edwards, Brent Mayhew, Wylie and goalkeeper Roy Bell, Waitemata have enough talent for the senior men to dream of one last big Cup push.
"You've got to believe it's possible." Wylie said. "We won't face many teams better than Central, but our feet are still firmly placed on the ground. We're not getting ahead of ourselves."
Waitemata now sit one win away from progressing to the nationwide quarter-final draw in the Cup for the first time in the club's history.
Standing in their way is Waitakere City, a side who have won 13 of their 14 games in the Northern First Division and are led by a player who even beats Wylie for experience.
Player/coach Jake Butler has racked up 200 appearances for Waitakere in the national league, 300 Northern League caps and three for the All Whites. He's also under no illusion how tough the Waitemata challenge will be.
"Waitemata have a lot of experienced players and are very well set up by Mayney," Butler said. "They have pace and some very good ball players. It will be a tough day.
"But we have a great bunch of lads who fight for each other and also have a real desire to win games. That, mixed with some quality players, has seen us do well so far."
By 5pm on Saturday afternoon, the new football kings of West Auckland will be revealed.
2016 Chatham Cup Round 4
Saturday 16 July
East Coast Bays vs Birkenhead United
2pm, Bay City Park
Forrest Hill-Milford United vs Bay Olympic
2pm, Becroft Park
Waitakere City vs Waitemata
2pm, Fred Taylor Park
Te Atatu vs Three Kings United
2pm, Te Atatu Peninsula Park
Universities vs Cashmere Technical
2pm, Ilam Fields
Queenstown Rovers vs Caversham
2pm, Queenstown Events Centre
Wairarapa United vs Miramar Rangers
5.30pm, Memorial Park (Masterton)
Sunday 17 July
Palmerston North Marist vs North Wellington
2pm, Memorial Park (Palmerston North)