Step 1

Heat oven to 400°F. Line rimmed baking sheet with parchment paper; insert wire rack.

Step 2

In small bowl, stir together vinegar, maple syrup, and oil.

Step 3

Stuff each date with 1 piece Manchego and 1 slice pepperoncini, then wrap with 1 strip prosciutto. Place, seam sides down, on prepared wire rack.

Step 4

Bake until cheese begins to soften, 6 minutes. Brush with vinegar mixture and bake until prosciutto is crispy and cheese is melted and warm, 6 minutes more.