Bring 1 cup raisins and 1/2 cup water to a boil in a pan over high heat. Reduce heat to medium-high; cook, stirring, until water has absorbed. Let cool; puree in a food processor. Cover and chill at least 1 hour.
Preheat oven to 350°F. Line a baking sheet with parchment. Whisk both flours, baking soda, salt and cinnamon in a bowl. Beat butter, oil, sugar and pureed raisins with an electric mixer on medium-high speed until smooth, about 3 minutes. Beat in eggs 1 at a time, then vanilla. Reduce mixer speed to low; beat in flour mixture. Stir in oats and remaining raisins.
Use an ice cream scoop or 2 tablespoons to form cookies; place 2 inches apart on baking sheet. Use moistened fingers to flatten to 1/2-inch thickness. Bake until cookies are golden but still soft, 18 to 20 minutes. Let cool on racks. Repeat with remaining dough.