In a large bowl, toss together the pear, plums, strawberries, cranberries, apples, 1/4 cup sugar and lemon juice until evenly combined. Set aside and allow to macerate for 30 minutes.
Heat oven to 350°F. Grease a 9-inch springform pan with cooking spray and set aside.
In a large bowl, beat together 1 1/2 cups granulated sugar, butter, orange zest and 100ml of the wine. The mixture won't come together smoothly at this point but that's okay. Beat in the eggs and vanilla. Add the flour, almond flour, and baking powder and stir until just combined but smooth.
Use a slotted spoon to scoop out half of the chopped fruit mixture and then add to the batter. Add 1 tablespoon of the liquid from the fruit and fold gently until evenly combined. Transfer the batter to the prepared pan and spread out into an even layer. Bake until golden brown and a skewer, inserted in the middle, comes out clean, 45 mins to 1 hour. Remove from oven and allow to sit in the pan for 15 minutes before removing the sides of the springform and flipping the cake upside down onto a plate or cake stand.
Once the cake is cool enough to handle, but ideally still a little warm, heat the remaining 50ml red wine and orange liqueur with the remaining 1 tablespoon granulated sugar in a small saucepan until melted, raise the heat and boil for a few mins until thickened and syrupy.
Pile the remaining fruit on top of the cake and arrange the sliced oranges, lemons and strawberries on top. Drizzle with the boozy syrup while still warm. Cut and serve with whipped cream. Enjoy!