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Preheat grill to high, using the two-zone method.
Whisk olive oil, balsamic, Worcestershire, and pepper together in a large bowl. Place all mushroom caps in the marinade, tossing to coat. Marinate mushroom caps for 30 minutes to one hour, tossing occasionally. Thread mushroom caps onto skewers, from side to side, so the top and bottom of caps will make contact with grill grates.
Place skewers on the hot side of the grill, with the tops down, reducing heat to maintain 375-400 degrees for 15 minutes. Turn skewers over and place them on the cool side of the grill. Continue cooking for another 30-40 minutes, checking after 20 minutes for desired caramelization. Remove from skewers and enjoy.
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