This chapter presents the second phase of my novel fair play argument which connects the class of fair play obligations identified in Chap. 3 to the broader project of redressing large-scale historic wrongs in a newly compelling way. In particular, I argue that while the normative force of externalist fair play obligations is sourced entirely in contemporary structural benefiting, they can nevertheless qualify as reparative in what I call an extrinsic sense, so long as the structural conditions that give rise to them bear the right kind of causal-historical relation to historic injustice generally. I begin by laying out Bernard Boxill’s classic account of the morality of reparation as essentially backward-looking, and work to show that despite my reliance on elements of Young’s forward-looking account of political responsibility, the obligations generated by my fair play approach can qualify as reparative in his sense. I support this claim by arguing (1) that despite appearances obligations to relinquish specific gains in the name of fair play are well interpreted under the paradigm of corrective justice, and (2) that those same obligations can qualify as reparative on Boxill’s account notwithstanding some notable differences between our two views.