This paper discusses how merchants or skippers suffering losses aimed to get redress of damages in trading and shipping from or with Holland and Zeeland in the fourteenth and early fifteenth century within the context of Anglo-Dutch trade and diplomacy. In concordance with legal doctrine both the English king and the Count of Holland considered reprisal as an ultimate remedy. Both rulers used the possibility of reprisal as a means of pressure within Anglo-Dutch diplomacy. Their willingness to support their subjects went beyond the issue of damage redress as it also enabled them to have more control over their subjects. When reprisal was eventually issued rulers on both sides of the Channel carefully supervised and controlled its procedure. Even though rulers were prepared to support victims via diplomacy and, ultimately, reprisal, they did consider individual interests of damage redress in function of the wider political and economic interests of their countries.