Preheat the oven to 400 degrees F. Slice off the top of the garlic head and wrap it in aluminum foil. Bake until soft, about 30 minutes. Squeeze out garlic and put aside.
Spread the roasted garlic and a generous dollop of goat cheese on each slice of bread and then place in the oven for a few minutes so that the cheese melts just slightly and the bread is warm.
To prevent the bread from sliding, place a touch of goat cheese in the center of each plate. Place the warm bread on top, then top the bread with a couple of slices pancetta. Next, top with the Swiss chard-lentil mixture and a spoon of the red wine sauce. Add a drizzle of Vincotto and the poached tomatoes.
For the lentils:
Cook the lentils in about 2 cups salted boiling water with the bacon, onion, carrot, and celery. Reduce the heat and let simmer, uncovered, for 30 minutes or until the lentils are tender. Drain the lentils; discard the vegetables and bacon and keep the lentils aside.
For the wine sauce:
Meanwhile, in another pot, bring the red wine, veal stock, and brown sugar to a boil. Reduce the heat and let simmer for 30 minutes, until reduced by half and thick, about 30 minutes. Season with salt and pepper, and keep aside.
For the crostini:
Meanwhile, in a hot pan, add 1/4 cup olive oil and grill the bread in in the hot oil on both sides for about 30 seconds. Finish in the oven for 5 minutes to crisp them. Put aside.
For the poached tomatoes:
Pour about 1 cup olive oil in a small stockpot. Heat the oil on medium and when hot, toss in the tomatoes. Remove when the tomato skin begins to crack, about 3 minutes. Remove the tomatoes, keeping the oil for another use.
For the pancetta:
Place the slices on a baking sheet covered with parchment paper. Cover with another piece of parchment paper and cover with another baking sheet to ensure they stay flat. Cook the pancetta in the oven for 15 minutes, or until crispy.
For the Swiss chard:
Add the butter to a hot pan. Add the Swiss chard and saute to heat through. Add the cooked lentils and heat gently on medium-low heat to warm through, then season with salt and pepper.