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Preheat oven to 450°F. Line two shallow roasting pans and/or 15x10x1-inch baking pans with foil. Cut one or two small slits in each tomato. Place tomatoes in a single layer in the prepared pans. Cut off the top 1/2 inch of garlic bulb to expose ends of individual cloves. Leaving garlic bulb whole, remove any loose, papery outer layers. Place bulb, cut end up, in a custard cup. Drizzle bulb with a little oil; cover with foil. Roast tomatoes and garlic on separate oven racks about 30 minutes or until tomato skins are blistered and garlic feels soft when squeezed; cool.
Coarsely chop tomatoes, discarding the loose skins and any excess juice. Squeeze the roasted garlic from individual cloves. Transfer tomatoes and garlic to a 6- to 8-quart stainless-steel, enamel, or nonstick heavy pot. Stir in wine, sugar, and salt. Bring to boiling over medium-high heat, stirring occasionally; reduce heat. Simmer, uncovered, for 15 minutes, stirring occasionally.
Press tomato mixture through a food mill fitted with a coarse die. (Or working in batches, transfer tomato mixture to a food processor or blender. Cover and process or blend until smooth. Press pureed mixture through a sieve.) Discard seeds and skins.
Return the strained mixture to the large pot. Stir in basil, oregano, black pepper, and crushed red pepper. Bring to boiling; reduce heat. Simmer, uncovered, for 45 to 50 minutes or until reduced to 8 cups. Remove from heat. Stir in lemon juice.
Ladle hot sauce into hot sterilized half-pint canning jars, leaving a 1/2-inch headspace. Wipe jar rims; adjust lids and screw bands.
Process filled jars in a boiling-water canner for 35 minutes (start timing when water returns to boiling). Remove jars from canner; cool on wire racks.