Preheat oven to 425 degrees F. In a large shallow baking pan toss pear slices with 2 tablespoons olive oil. Roast 20 to 25 minutes or until very tender. Cool slightly.
Spread all bread slices with pepper jelly. Layer 4 of the bread slices with ham, roasted pear slices, and cheese. Top with remaining bread slices, spread sides down. Brush both sides of each sandwich with additional olive oil.
Heat a large skillet or griddle over medium heat. Cook sandwiches 2 to 3 minutes or until bottoms are golden and cheese is melted, turning once halfway through cooking.