Place garlic in a small ramekin, drizzle with 1 tablespoon olive oil, and wrap in foil. Bake until soft, about 45 minutes. When cool enough to handle, squeeze garlic flesh from head into a small bowl.
Arrange tenderloins on work surface. Rub the top each tenderloin with 1/2 of the roasted garlic and season with salt and pepper. Mix together the herbs and scatter half of the mix over the garlic on each tenderloin. Wrap 6 strips of bacon around each tenderloin and tie bacon in place with kitchen twine.
Heat oven to 375 degrees F.
Heat oil in a medium, skillet over medium-high heat. Sear the tenderloins until golden brown on all sides. Transfer seared tenderloins to medium roasting pan; place in the oven and cook to medium doneness about 8 to 10 minutes. Transfer tenderloins to cutting board and let stand 10 minutes. Remove twine before carving.