Preheat oven to 375°F. Cut the squash in half and discard seeds. Slice squash about ½ inch thick and toss with 1 tablespoon olive oil. Arrange on baking sheet and place in oven while you make the glaze.
In a small saucepan over medium heat, add remaining olive oil. Add garlic and sauté until golden brown. Add the rest of the ingredients and whisk to fully incorporate. Simmer until liquid reduces by about half and becomes syrupy, about 10 minutes.
Remove squash from the oven and flip the pieces, then brush a generous portion of glaze over each. Return pan to the oven and cook another 20 minutes or so, until squash is tender