The Cordwainer/Shoemaker was different from the Bootmaker. Cordwainers used Cordovan leather from Spain because it was softer and made better shoes for those who could afford it.So this would have been imported.
Apprenticeships could either be via the family ,father to son etc or by being apprenticed to someone outside the family. Apprenticeships often lasted 7 years with some boys never achieving their skill.
Apprentice Records for your ancestor may be found in the local record office to the county where he lived if these have survived.
If this was a family apprenticeship then probably no documents would ever have been generated. Do not forget to trace Poor Law apprentice records as young boys were often put out to work in this way to save the overseers of the parish having to pay the additional burden of their upkeep .
Hope this helps.