The West Midlands Mayor accused the Government of making the "wrong decisions" on the distribution of the £2.1billion Levelling Up Fund, which saw the region miss out on millions of pounds of investment.
He told the Star he had already had "positive talks" with Levelling Up Secretary Michael Gove, who had said there was a "legitimate debate" over how funding was allocated in future.
Mr Street has called for an end to Whitehall's "bidding and begging-bowl culture", saying funding was currently being allocated in a "very stupid" way when it should be devolved to local decision makers.
And he has revealed the two West Midlands bids he thinks were most unfortunate to miss out.
The Conservative Mayor said: "I was extremely disappointed and I thought the wrong decisions were made.
"We had a lot of bids that did not get through, some of which I know were really first class and were for things that were really important for the future of each area.
"The fact that Dudley Council has not received anything in two rounds of levelling up cash, I just cannot understand how that can be right.
"Birmingham's bid for The National Centre for the Decarbonisation of Heat at Tyseley was certainly one I thought was really strong. What can be more important at the moment than the issue of making domestic heating more efficient?
"It was about getting us at the centre of a new technology, and I can't understand why that did not get support. I also thought the Bilston bid (for a health and regeneration centre) was really important.
"I think that really hit home on some of the underlying issues that could determine the area's future success.
"When I see some of the bids that did get through, I can't see why these were not competitive."
Across the West Midlands Combined Authority (WMCA) area just two out of 17 bids were successful, with Walsall Council getting £20m towards the regeneration of Willenhall and Sandwell Council receiving £20m for a new leisure centre in Cradley Heath.
Mr Street said he had held "positive talks" with Mr Gove, who had acknowledged there was a legitimate debate about how cash was allocated.
"The underlying point is that this seems to me a very stupid way of allocating the money," he added. "Civil servants in London are taking decisions on community projects and I can't see how they can make good judgments between one project and another.
"A far better way of doing this is to allocate money locally."
Michael Fabricant, Conservative MP for Lichfield, said devolving funding to local areas was "not the answer".
He said: "The total value of the most recent Levelling Up Fund – £2.1billion – would spread very thinly across all the authorities in the United Kingdom if it were to be devolved in that way.
"It would not make the big differences that levelling up awards are meant to make.
"With just over 100 projects chosen in the current round with an aim ‘to create jobs and boost economic growth’, there were always going to be winners and losers."