Heat 1 tablespoon olive oil in a medium saucepan over medium heat. Add wild rice and sauté until a nutty aroma emanates, about 2 minutes.
Add 1 1/2 cups chicken stock, bring to a simmer, then reduce heat to low, loosely cover and simmer until rice is tender (and grains curl open), about 40 minutes. If stock is absorbed, add 1/2 cup more.
Remove cooked wild rice from the pot.
Return the pot to medium heat and add remaining 2 tablespoon oil. Add onion, celery and carrot and sauté until onion is translucent, about 5 minutes.
Add Arborio rice and stir to coat, 1 minute. Add wine and stir until absorbed. Add 1/2 cup chicken stock and stir until absorbed (you can reduce heat to low and then you can walk away from the pot for a minute or 2).
Add thyme and sage and add more stock and stir until absorbed and rice is cooked (when rice is cooked it is still al dente).
Stir in cranberries, pumpkin seeds and reserved wild rice. Stir in Asiago until melted and season to taste. Let risotto cool slightly.
Preheat oven to 190°C. Cut tops off of tomatoes (keeping) and spoon out seeds. Spoon risotto into each mini tomato until heaping and top with cap.
Bake for 15 minutes, just to soften tomatoes, and then serve.
Mini tomatoes can be served as hors d’oeuvres or snacks, or filling makes 6 to 8 larger tomatoes for a great side dish.