Prep & cook time: 1 hour. If making up to 1 day ahead, prepare through step 5; cover and chill. Let warm to room temperature and unmold.
**6-8 ramekins 1/2 - 3/4 cup size (I used Pyrex)
1. Cut bread into 1/2 inch chunks. In a food processor or blender, whirl into coarse crumbs; you should have about 2/3 cup.
2. Rinse zucchini and trim and discard ends. Cut into 1/8 inch thick rounds.
3. In a large (5-6 qt) saute pan over medium heat, stir bread crumbs often until golden and crisp, about 5 minutes. Pour into bowl.
4. Add 3 tablespoons olive oil to pan and increase heat to medium-high. stir in zucchini, garlic, chopped oregano, salt and pepper. Cover and cook, stirring occasionally, until zucchini begins to soften, about 5 minutes. Uncover and stir often until zucchini is browned and soft when pressed, 7-10 minutes longer. Remove from heat and stir in toasted crumbs, the parmesan cheese and more salt and pepper if needed.
5. Generously oil 6-8 ramekins with olive oil. Divide zucchini mixture evenly among ramekins and press in firmly. Let stand at room temperature at least 5 minutes, up to four hours.
6. Rinse and core tomatoes. Cut crosswise into 1/4 inch slices. Arrange 3 tomato slices on salad plate. Run a knife around the inside edge of ramekins and invert zucchini timbales onto tomatoes; if necessary, hold each ramekin and plate together and shake gently to release. If desired, garnish with oregano sprigs. You may drizzle some olive oil over the tomatoes if desired and salt and pepper those to taste also.