In a large heavy saucepan, heat 2 tsp of olive oil over medium heat. Fry the bacon, turning once, until crispy. Transfer to a paper towel-lined plate. Let cool, then crumble.
Add one tablespoon of olive oil to the pan. If using regular bacon, you can omit the olive oil, and drain all but one tablespoon of fat from the pan instead. Add the onion and cook until softened, about 4-5 minutes. Stir in the garlic, and the spices and let cook for about a minute.
Stir in the tomatoes and pumpkin, bring to a boil, reduce heat to low and let simmer for 20 minutes. Remove from the heat and let cool slightly. Using either an immersion blender or regular blender, puree the soup until smooth. If using a regular blender, work in batches, remove the stopper from the lid of the blender and place a thick towel over the hole, holding it in place with your hand as you blend.
Place the pan back onto the heat, add the heavy cream and bring to a simmer, then serve topped with the crumbled bacon and a grind of black pepper.