Two Dragons Competing for the Jewel is a depiction not of dragons but of gnarled branches of old pines reaching from either side of the painting and twisting like cork screws, their ends shaped to suggest the heads of bird-like dragons. Between the two pines is a full moon set against a cloud-streaked sky. The glowing moon suggests the prize the rival dragons seek, traditionally a precious jewel.

Isabella received this painting as a gift from Josephine MacLeod, who gave it as a memento of their mutual friend, curator and scholar Okakura Kakuzo. Both women believed the painting to be Okakura's work, and it was added to the Chinese Room in his honor. Unknown to Isabella, this was her second work by Yokoyama Taikan, one of Okakura's best students and one of Japan's most famous modern painters, the first being the sketch he painted of chrysanthemum leaves in her guest book when he visited her with Okakura in 1904.