After three failed attempts at winning promotion via the play-offs in the past four years, Winkelman is prepared to give Robinson one of the biggest transfer budgets in the club's history to try and bring Championship football to Milton Keynes.
But Winkelman admits it could be win or bust. If Dons are not promoted next season, the chairman will have to drastically tighten his belt.
"There is more pressure on this side to get promoted than any other before. I will not be happy with the play-offs like I have been in the past - it's got to be automatic promotion this season," Winkelman told the Dons Supporters Association AGM on Tuesday night.
"I know Karl will make a real go of it this season. This represents our best ever chance of getting out of League One and into the Championship, where the club can take the next step in developing.
"But if it doesn't happen this season, then we might have to consolidate for a year to build back up for the following season."