From tragedy to humiliation, a banishment that signalled the beginning of the end of a chaotic ZIFA board and to the ignominy of losing to the world's weakest football nation.
And, there was even that bizarre episode where the career of a thoroughbred radio and television football commentator was briefly put on hold.
The Warriors' romance with World Cup qualifiers, since the turn of the millennium, has been a very rocky affair.
And, unless they turn around one of their worst defeats tomorrow, by not only beating but eliminating global lightweights Somalia, a very bad situation could even turn worse.
A few months ago, that should have been quite an easy task and the question, really, would have been about the number of goals the Warriors would score in the feast.
But, since the fallout of their AFCON finals appearance, where they arrived with high hopes before the demons of the chaos of their camp squashed those dreams, things have changed.
Their caretaker coach, taking charge of his first World Cup qualifier, and their entire team, playing at this stage for the first time in their careers, received a baptism of fire last Thursday in Djibouti.
A 0-1 loss to Somalia was as bad as things can get at this level of the game because, until then, the homeless Ocean Stars had never won a World Cup qualifier.
After all, this is a troubled country where football has taken a back seat for decades as it dealt with the ravages of civil strife and an Islamic insurgency.
Even its main football stadium was, for years, converted into an operational centre for African troops who arrived to quell the insurgency.
For 29 years, Somalia didn't even send a representative to the CAF inter-club tournaments until Mogadishu City Club took part in the CAF Confederation Cup in July.
Told to look for an alternative venue to host their home leg of the match, because of security concerns, they chose to play it in Zanzibar.
The irony was that their opponents, Malindi, were also from Zanzibar and that meant they played both matches at home and, as expected, sailed through.
Given Zanzibar were also only admitted into the CAF family, as a member, two years ago, Malindi's 1-0 aggregate win didn't raise eyebrows and their elimination, at the next hurdle, was also expected.
Had everything gone according to plan, the battle between the Warriors and the Ocean Stars would have been settled yesterday at Barbourfields.
But, then, nothing goes according to plan when it comes to Somalia and their failure to secure flights into Zimbabwe at the weekend forced the postponement of the decider to tomorrow.
The world will be closely following the events at the National Sports Stadium where, on the grass of the giant facility and not the artificial surface in Djibouti, the Warriors are expected to win.
The challenge, however, is that the Warriors have never won a World Cup qualifier in 11 years since that day at Rufaro when Gilbert Mushangazhike scores twice in a 2-0 win over Namibia.
And, this is a lightweight Warriors side without some of its heavy hitters like Knowledge Musona, who called the team management while they were in Djibouti, to rally the side not to blow this World Cup opportunity.
There also appears to have been a climb down on the hard-line stance that saw some of the team's regulars, and leaders, being sidelined from the battle in Djibouti.
Ovidy Karuru, one of the three captains of the Warriors at the AFCON finals, was set to arrive in Harare yesterday to join the team for tomorrow's battle.
ZPC Kariba defender Ian Nekati has also been roped into the squad.
Khama Billiat, who had initially been reported to be available for tomorrow's game, will not feature as he continues to battle with an injury he sustained in Cape Town.
Italian gaffer Landi Roberto, who once coached Liberia, is also set to watch the match amid reports of negotiations for him to consider taking over as substantive coach.
He is set to arrive in Harare today.
The Warriors simply can't afford another boob -- even though their history with the World Cup qualifiers, in this millennium, doesn't provide their fans with both comfort and optimism.
For it was in these qualifiers when tragedy struck, at the giant stadium, in 2000, during a World Cup qualifier against Bafana Bafana, leaving 13 fans dead.
It remains the darkest day in the history of Zimbabwe sport.
Then, a few years later Jay Jay Okocha and his Super Eagles came to town and, after toying around with the Warriors, comfortably won that World Cup qualifier 3-0.
Charles Mabika, seduced by the artistry of Okocha while commentating on the match, was deemed to have overdone his lyrical portrayal of the Nigerian superstar.
And, his commentating career, was briefly put on hold.
The reverse fixture in Nigeria turned into a humiliation as the Warriors lost that match 1-5.
Six years ago, long before the world had known Mohamed Salah as it does now, the Egyptian forward came to the giant stadium and scored a hat trick in a 4-2 victory for his nation.
Musona and Lloyd Zvasiya replied for the Warriors in that World Cup qualifier on June 9, 2013, during a group phase that saw Zimbabwe fail to win even one of its six matches.
Then, two years later, FIFA barred the Warriors from the 2018 World Cup qualifiers over the Valinhos affair.
That triggered the beginning of the end of Cuthbert Dube and his ZIFA board as they were soon swept away in elections that followed.
The World Cup banishment made headlines around the world, just as their return to the tournament last Thursday did, following their shock loss to Somalia.
Now, should they fail tomorrow, more global negative headlines will follow and their fractured romance with the World Cup qualifiers, which have delivered more pain than joy, will continue.