Chop enough sage to equal 1 tablespoon; set aside remaining sprigs. Combine squash, chopped sage, 2 tablespoons olive oil, 1/2 teaspoon salt, and pepper in a large bowl. Spread out in a single layer on a large jellyroll pan. Turning once halfway through, roast squash 30 to 35 minutes, until tender and caramelized.
Meanwhile, line a large plate with paper towels. Remove stems from remaining sage. Pour 1/2 cup olive oil into a small skillet over medium heat. Fry 1/3 of sage leaves 20 to 30 seconds, until crisp. Remove from oil with slotted spoon and drain on paper towels. Sprinkle with salt. Repeat process with remaining sage.
Arrange squash on a platter and garnish with fried sage leaves.