Preheat the oven to 350 degrees F. Line a rimmed baking sheet with parchment paper.
Add the strawberries, oil, 2 tablespoons of the sugar and a pinch of salt to the prepared baking sheet. Toss well to coat evenly and spread out on the baking sheet. Roast until the strawberries are soft and have released some of their juices, about 30 minutes. Pour the strawberries and the juices into a bowl and toss with the wine. Allow to cool to room temperature.
Meanwhile, in a medium bowl, whisk the heavy cream with the mascarpone and the remaining 3 tablespoons sugar until soft peaks form, about 3 minutes.
To serve, divide the strawberries among small serving cups or coupes. Dollop with the cream and sprinkle with some of the cookie crumble.