Preheat the oven to 450 degrees. Remove the ends of the squash, and then cut it in half. Remove the seeds, and slice into ½-inch wedges cross-wise. When you roast it, the skin will be soft and edible. Place on a parchment paper-lined baking sheet. Toss with 1 tablespoon of olive oil and a good sprinkling of salt and pepper. Cook for 30 minutes, flipping once, halfway through, until tender and golden brown. Allow to cool slightly.

Wrap each tenderloin with 1 piece of bacon. No need to season them with salt first, but you can lightly if you want. In a large pan, add a little oil, and then place the bacon wrapped chicken on top. Cook in batches if necessary. Over medium heat, cook on one side for 6 minutes. Allow the bacon to develop a crust and become easier to flip without sticking. Turn, crisp on the other side for 4-5 minutes or until chicken is thoroughly cooked. Drain on a paper towel lined plate, then cover with aluminum foil to keep warm.

Make dressing by whisking white wine vinegar, mustard, olive oil, salt and pepper. Place chopped romaine and sliced peppers on a plate or platter. Drizzle with dressing. Put cooled acorn squash slices on top. Serve with warm chicken tenderloins.