Combine 3/4 cup mint, the panko or matzo meal and 2 tablespoons olive oil in a medium bowl. Add the minced garlic, 1 teaspoon rosemary, the red pepper flakes and 1/2 teaspoon salt and mix until combined.
Unroll the "tail" of each lamb chop (the long thin section folded around the chop). Season the lamb with salt, then press the crumb mixture under the tail section; roll up the tail around the filling and secure with kitchen twine. Put the chops on a plate, cover with plastic wrap and refrigerate 2 to 4 hours.
Preheat the oven to 450 degrees F. Remove the lamb chops from the refrigerator 20 minutes before cooking. Make the tomato-mint jam: Toss the tomatoes, whole garlic clove, 1 tablespoon olive oil and the remaining 1 teaspoon rosemary on a rimmed baking sheet. Transfer to the oven and roast until the tomatoes are slightly charred, 15 to 20 minutes; let cool slightly, then transfer to a medium bowl. Add the vinegar and sugar and mash with a fork until somewhat smooth. Stir in the remaining 1/4 cup mint and season with salt.
Heat a skillet over medium-high heat. Add the remaining 1 tablespoon olive oil; sear the lamb chops until browned, about 3 minutes per side. Using tongs, turn the chops onto their sides and sear until the fat browns, about 2 minutes. Transfer to a rimmed baking sheet; roast in the oven until a thermometer inserted into the center registers 140 degrees F for medium rare, about 10 minutes. Let rest 5 minutes; remove the twine and serve with the tomato-mint jam.