Preheat oven to 375°F.
Place strawberries, vinegar and sugar in large bowl and toss together.
Spread onto a baking sheet lined with parchment, in a single layer, and drizzle with oil.
Roast strawberries for about 20 to 25 minutes, until slightly shriveled and beginning to juice (you’re lightly roasting the strawberries).
Allow strawberries to cool, about 20 minutes.
Pour strawberries, pound cake, ice cream, and milk into a blender, cover and blend until smooth.
Pour into two glasses and top with a dollop of whipped cream and a sprinkle of pound cake crumbs. Serve immediately.