How to Make It
Preheat the oven to 300°. Spray a 9-by-13-by-2-inch glass baking dish with vegetable oil spray. Line the dish with aluminum foil, making sure to press it into the corners; spray the foil.
In a standing electric mixer fitted with a paddle, beat the feta with 1 1/2 cups of the sugar and the flour at medium-low speed until creamy. Add the cream cheese and beat until blended. Add the whole eggs and egg yolks, one at a time, beating well between additions; scrape down the side of the bowl as necessary. Beat in the heavy cream. Pour the cheesecake mixture into the prepared baking dish.
Set the dish in a large roasting pan. Add enough warm water to the pan to reach halfway up the side of the dish. Bake on the bottom rack of the oven for about 1 hour, until firm and set. Transfer the baking dish to a rack and let the cheesecake cool to room temperature. Chill the cheesecake in the freezer until very firm, but not frozen solid, 3 to 4 hours.
Meanwhile, in a large saucepan, combine the red wine with the vanilla bean and seeds, peppercorns, lemon juice and the remaining 3/4 cup of sugar and bring to a simmer over moderate heat. Add the dates and simmer until plump, about 10 minutes. Transfer the dates to a bowl and boil the liquid until it has reduced to 1 cup, about 10 minutes. Let the syrup cool completely, then strain it over the dates.
Preheat the oven to 350°. Brush one sheet of the phyllo dough with melted butter. Cover with a second sheet and brush with butter. Repeat with the remaining 2 phyllo sheets, buttering between them. Cut the layered phyllo into 3-inch squares (you should have 24). Transfer the squares to a large baking sheet. Cover with a sheet of parchment paper and top with baking sheet to keep the phyllo flat. Bake for about 15 minutes, until golden and crisp. Remove the top baking sheet and let the phyllo squares cool.
Invert the chilled cheesecake onto a cutting board and peel off the foil. Using a hot, moist knife, cut the cake into twelve 3-inch squares. Set a cheesecake square on each of 12 phyllo squares and top with the remaining squares. Transfer the cheesecakes to plates. Drizzle some of the red wine syrup around each plate and garnish with the dates.