But he was pleased with the outcome all the same.
The draw was made live on Radio Sport yesterday and, coincidentally, the four Auckland clubs, two Wellington teams and two South Island sides drew each other.
Caversham has drawn an away fixture against Christchurch club Ferrymead Bays on July 24, Miramar Rangers hosts Wellington United, Forrest Hill Milford is at home to Auckland league heavyweight Bay Olympic, and 2008 champion East Coast Bays hosts Glenfield Rovers.
Fleming, who tuned in to hear the draw, was not entirely won over by the process.
"They go to great lengths to tell us this isn't rigged before they have even pulled a name out.
Then it goes bang, bang, bang all the Auckland teams play each other, the Wellington teams play each other and we go to Christchurch," he said.
The validity of an earlier live draw was also questioned when a preliminary schedule was discovered which also paired Dunedin Technical and Caversham.
Footballsouth operations co-ordinator Peter Ritchie explained it at the time saying an automatic programme had generated the preliminary schedule and it was just a coincidence it also paired the Dunedin teams.
But enough people saw the preliminary schedule before the official draw to set the rumour mill into motion.
And a botched draw, which had Roslyn-Wakari making an expensive trip to play Nelson, had to be re-drawn after New Zealand Football acknowledged it had mistakenly lumped Footballsouth and Mainland together before the scheduled merge in round four.
Regardless of his concerns, Fleming was thrilled his side had drawn surprise quarterfinalist Ferrymead Bays.
"Christchurch Tech are the form team up there.
And Nelson are difficult to play in Nelson.
But they [both] got bumped out early on.
Not that Ferrymead are there by default.
They have some decent players, but I'm sure a lot of teams would have been looking to play Ferrymead."
"You've got to be happy we've avoided some of the bigger teams," he added.
Caversham brushed aside fellow Dunedin club side Roslyn-Wakari 8-2 in round four, while Ferrymead defeated Western 4-3 in a penalty shoot-out.
Bay Olympic and East Coast Bays shape as the sides to beat, and three-time winner Miramar Rangers remains a threat.
But Caversham has been in good form, particularly on attack.
With a bit more resolve on defence, Fleming believes his side has as good a chance as any team.
"Our finishing has been excellent... but we've let in a few goals as well, which is a concern. But it is good to know we are capable of scoring goals. Now we just have to work on not giving anything away."
