But the ebullient Fleming fancies his team's chances against fourth-placed Auckland, which has had several changes in coaching staff and senior players from last year.
Make no mistake, Oceania League winner Auckland will be strong, but the winds of change are blowing through its Kiwitea St Stadium.
New coaches Aaron McFarland and Ramon Tribulietx in three matches have lost to Waitakere 3-1, had a scoreless draw with Wellington and scratched in 3-2 over Waikato.
Otago has lost its two openers, at home to Waikato 1-0, and away to Hawkes Bay 3-2, but in the absence of warm-up matches, Fleming now knows his players better and feels his side has improved in every game.
"We really should have got the points from the Bay after we went ahead 2-1 in the second half, but some defensive lapses cost us dearly," he said.
Once again, Andy Coburn is struggling for full match fitness but there are hopes he will play, as his physical presence, combined with Paul Seaman and the in-form Nathan Knox, could make an effective triangle in midfield.
Striker Phil Ruggles is still adjusting but had a very good second half and set Seaman up expertly to take his goalNew signing Matt Thomas stood out with an industrious performance.
He may yet add another string to Otago's bow since he had professional trials in England as a young goalkeeper and could be a useful back-up between the sticks.
Team manager Aaron Burgess was a surprise signing this week, changing his status to reserve striker, and he emerges as yet another playing option in the travelling squad. His situation is similar to that of Hawkes Bay manager/reserve Chris McIvor, who went on and scored a 90th-minute winner to beat Manawatu 1-0.
"We have to be smart and get the maximum benefit from our restricted travelling squad. Especially since we will soon lose captain Tim Horner and youth coach Richard Murray for a few weeks when they take the Otago under-15 group to Singapore for 10 days."
United's obligatory two youth players on the team card may get their chance in starting line-ups if Fleming's squad gets any leaner.
"Those youth players who were keen enough to train regularly with the first team are now close to senior pace, and if they get a chance I am sure they will acquit themselves well, since they now know the team pattern and the jobs that need done."
Former Otago player Stu Kelly will line up for Auckland, as will the highly-rated David Mulligan, who has more than 200 appearances in the English league alongside his 25 New Zealand caps. He also has experience with Wellington Phoenix.
Fleming said the side would have to show plenty of energy to get a favourable result.
In the ASB Youth League, Otago United plays away to Manawatu tomorrow, eager to bounce back from last week's 7-1 loss to Canterbury.
Auckland City hosts Waikato FC and Hawkes Bay United faces Waitakere United in Northern Conference fixtures. Canterbury United hosts Team Wellington.
OTAGO UTD v AUCKLAND
- Auckland, 3pm tomorrow
Otago United: (from) Adam Highfield, Tristan Prattley, Matt Thomas, Hayden Gunn, Tom Sadd, Nathan Knox, Paul Seaman, Anthony Hancock, Phil Ruggles, Andy Coburn, James Reichwein, Harley Rodeka, Tim Horner (captain), Tom Connor, Cam Burns, Liam Lockart, Matt Brook.
Auckland: (from) Jacob Spoonley, Angel Berlanga, Ian Hogg, Sam Campbell, Phil Edginton, Stu Kelly, James Pritchett (captain), David Mulligan, Daniel Koprivic, Matthew Upton, Alex Fenedris, Adam Dickinson, Adam McGeorge, Daniel Morgan, Adam Thomas, Aaron Bawdekar.