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Pre-heat oven to 300 degrees. Line a baking sheet with foil or parchment paper to catch the drippings from the crackers and place a cooling rack on top the lined baking sheet.
To prep, thinly slice parmesan wedge and set aside. Slice the bacon into fours so they match the length of the crackers. To assemble, place one piece of parmesan onto the cracker, top with bacon, followed by the brown sugar, and finally the red pepper flakes. Repeat with remaining crackers.
Place each cracker onto the cooling rack side by side. Bake in the oven for 35-45 minutes, rotating the pan halfway through and begin checking on them at 30 minutes. Once the bacon is cooked through and the edges of the crackers begin to brown, they are finished.
Serve warm or at room temperature.