The present invention is a new and distinct double cropping red raspberry cultivar named ‘Diamond Jubilee’, which is capable of producing high yields of large, bright colored, sweet and exceptionally firm fruit that has positive consumer appeal characteristics. The cultivar is characterized by its high cane vigor, large leaves, its low acidity, sweetness and firmness and its fruit morphology, specifically its broad conical shape. ‘Diamond Jubilee’ plants are also outstanding in that they produce commercial quantities of large, firm and flavorful fruit with long postharvest life in both the overwintering floricanes and late summer primocanes.