In a 2-cup measuring cup or a medium bowl whisk the syrup, oil, vinegar and cayenne pepper until emulsified.
Pour the dressing over the sprouts, reserving one-quarter cup of the dressing to use later.
Cover your baking sheet with a silicone mat or parchment paper and place the Brussels spouts evenly over the sheet, cut side down. Bake at 450°F for about 15 minutes until the sprouts are fork tender and the underside is turning brown.
While the sprouts are roasting, fry the bacon in a sauté pan until crisp.
Place the crispy bacon strips on a paper towel to absorb the grease and set the bacon aside.
Remove the pits from the dates and dice the dates into tiny bits.
When the sprouts are ready, place them in a bowl and crumble the bacon over the top of them. Add the dates and remaining dressing and toss to combine.