The question of the presence and role of Plato in the work of Jacques Derrida has received little attention in comparison to discussions of Derrida’s relationship with other philosophers in the literature. On consideration of the fact that it is Plato’s formulation of binary oppositions in relation to which Derrida initially deploys deconstruction, the absence of scholarly discourse to this end proves puzzling. This thesis responds to this lack by undertaking the first extended examination of Derrida’s textual encounters with Plato which includes a discussion of both the earlier and later periods of Derrida’s work. I begin by providing a working definition of deconstruction, albeit under the proviso that such a definition may not be possible. I argue that if one takes Derrida’s own pronouncements on deconstruction into account, then deconstruction is to be understood as more akin to the concept of autoimmunity as it emerges in Derrida’s later work. I argue that this is the case inasmuch as Derrida’s formulation of autoimmunity accounts for the absence of a controlling agent who dictates the course that a deconstructive reading of a text should take, and instead shifts focus onto the manner in which a text ultimately deconstructs itself. I then proceed to a series of readings of select pieces of work from the Derridean corpus in which Derrida encounters Plato both exclusively and in the course of a discussion of other philosophers in the Western canon. I undertake a discussion of Derrida’s reading of Phaedrus in ‘Plato’s Pharmacy’, arguing that Derrida mimics Plato’s authorial movements in that essay, inasmuch as both philosophers may be viewed as vying for control of the figure of Socrates as he appears within that dialogue. Specifically, I argue that Derrida’s fixation on the polysemic quality of the pharmakon as it is used by Plato in the Phaedrus eventually affords him an opportunity to associate Socrates with writing, in counterpoint to Plato’s apparent intentions within the dialogue itself. I argue that in so doing Derrida appropriates Socrates from Plato’s control at the moment when his mimicry of Plato reaches its zenith, and that this mimicry reveals a proximity between Derrida and Socrates that repeats itself in Derrida’s later encounters with Plato. Following this, I present a reading of ‘Khōra’ in which Derrida discusses the eponymous entity as it appears in Timaeus. From this reading I conclude that Derrida appropriates certain characteristics of Socrates within his modus operandi, particularly the deployment of elenchus as well as an attendant preoccupation with paradox and aporia in the texts that he reads. I argue that, in response to Socrates’ relative absence from Timaeus, Derrida’s rigorous interrogation of the dialogue, his description of khōra as atopic, and his subsequent revelation of the aporetic repetition of khōra in various forms throughout the dialogue may be seen to result in the discomfiture of the dialogue itself, in much the same way that Socrates’ movements are described by Plato as being deployed along similar lines and to the same end. Turning to a discussion of Derrida’s later ethico-political forays, I argue that Plato may be seen to attend Derrida’s positions in The Politics of Friendship and Rogues, inasmuch as Derrida’s discussion of friendship and democracy is heavily influenced both by Plato’s implicit presence and by Derrida’s prior formulation of khōra in the eponymous essay. In particular, I argue that the hypothetical formulation of a democracy devoid of brotherhood given by Derrida at the end of The Politics of Friendship is evocative of Plato’s formulation of friendship in the Lysis, and that Derrida’s association of the ‘democracy to come’ with khōra in Rogues results not only in a redeployment of the Socratic arsenal on Derrida’s part, but also of the continued repetition of khōra as deconstructive structure therein. Finally, I argue that my discussion of Derrida’s work as it appears in the thesis is indicative of a relationship between Derrida and Plato that is subtle, complex, and convoluted, in contrast to the commonly held notion that Derrida simply opposes himself to Plato, and that the relationship between the two philosophers is simply one of opposition and antagonism. Rather, I conclude that Plato is at once Derrida’s opponent as well as a figure from which he borrows certain qualities, that Plato represents a point from which Derrida departs as well as a point to which he returns repeatedly, and that this results in a relationship that can only be described as aporetic.