Preheat oven to 450 degrees and line baking sheet with parchment paper. Toss fennel with 1 tbsp oil, salt, and pepper, and place onto baking sheet in a single layer. Bake for 13-15 minutes, or until fennel is caramelized. Let fennel cool to room temperature.
Add the Breton Gluten Free Original with Flax crackers to a food processor and pulse until fine crumbs are formed (yield: roughly 3/4 cup crumbs). Heat remaining 1 tbsp oil in a medium saucepan on medium heat. Add crumbs and stir frequently until crumbs are golden brown and crispy, about 5-7 minutes.
Meanwhile, add arugula, fennel, and cheese to a large bowl. Add dressing and toss to combine. Before serving, top with breadcrumbs and fennel fronds for garnish.