The aim of this study is to determine the intertextual references in the short story Tarquin of Cheapside by F. Scott Fitzgerald and evaluate Turkish translations of the contexts with intertextual references. To this end, the original short story was analyzed based on the intertextuality theory by Riffaterre (1978; 1983; 1990). With the “hypogram” of the short story established as coined by Riffaterre (1978), “ungrammaticalities”, another term coined by Riffaterre (1978), were determined in the short story and these ungrammaticalities were classified as ordinary intertextuality and obligatory intertextuality, the major concepts in Riffaterre’s intertextuality theory according to Aktulum (2011). The results of the interxtuality analysis revealed that the short story “Tarquin of Cheapside” is intervowen with cultural and literal intertextual references, and ordinary intertextual references were far surpassed by obligatory intertextual references. For translation analysis, the contexts with intertextuality in the original short story were compared to a Turkish translation of the short story based on Öztürk Kasar’s (Öztürk Kasar and Tuna, 2015; 2017) “Systematics of Designificative Tendencies in Translation”. The results of the translation evaluation showed that translators might resort to certain designificative tendencies in rendering a literary work into another language. Since intertextual references might be culture-specific at times, the translators of literary works might deliberately or indeliberately resort to certain designificative tendencies. Here lies the contribution of semiotics of translation to literary translation in that if the translators indeliberately use designificative tendencies, they could explain their preferences with a thorough awareness of designificative tendencies, on the other hand, if translators deliberately use designificative tendencies in their literary translations, they know when and how to apply those designificative tendencies. Therefore, semiotics of translation serves as a guide to professional or prospective literary translators in making sound decisions in translation process.