Place the head of garlic on a small piece of foil and drizzle lightly with the olive oil. Season with salt and pepper and then enclose the garlic with foil. Place in the center of a lightly oiled or sprayed, rimmed baking sheet.
Surround the garlic with the tomatoes. Drizzle olive oil over the tomatoes and season with salt and pepper.
Bake in preheated oven for 1 ¼ hours until the tomatoes are caramelized and juicy.
Add blended tomatoes and garlic to a 4 qt. saucepan. Add remaining ingredients to pan and simmer for about 20 minutes on low until the jam thickens and coats the back of a spoon.
Cool and store in a wide mouth mason jar or container.
*refer to blog post for image on cut garlic** triple concentrate tomato paste comes in a tube and solves the problem of opening a can and having to freeze or pitch the rest.