Preheat oven to 350 degrees and line a baking sheet with foil. Lightly spray with non-stick spray and set aside.
Unroll the crescent roll dough and separate each triangle.
Lightly brush each triangle with olive oil then lay a half slice of Provolone cheese and a half slice of cheddar on the large side of the triangle. Top with two asparagus spears, roll-up, then lay on the prepared baking sheet.
Repeat for the remaining triangles.
Bake for 15-18 minutes or until golden brown.
Once done, remove from oven, drizzle with olive oil and sprinkle with Italian seasoning.