Wrap each pineapple spear with one bacon slice. Lay seam side down on a wire rack set inside a large foil-lined baking sheet. Repeat with remaining pineapple spears.
In a small bowl, add brown sugar and soy sauce. Stir to combine. Brush on each pineapple spear.
Bake for 20-25 minutes until bacon is cooked and beginning to crisp.