If i understood you right, you want to get 10 most recent Documents fron a specified customer?
That's easy.
NSFetchRequest *request = [[NSFetchRequest alloc] init];
request.entity = [NSEntityDescription entityForName:@"Document" inManagedObjectContext:managedObjectContext];//Specify the entity Name
request.predicate = [NSPredicate predicateWithFormat:@"customerID = %@",customerID];//Specify the ID you need
request.sortDescriptors = [NSArray arrayWithObject:[NSSortDescriptor sortDescriptorWithKey:@"updatedDate" ascending:YES]];//Sorted by most recent ones
request.fetchLimit = 10;//You'll get ten latest Documents
NSError *error = nil;
latestDocuments = [managedObjectContext executeFetchRequest:request error:&error];
EDIT
As we found out, that the task is to get ten most recent documents, but just one per customer, i really see no way to do this somehow efficient(i mean,without IN query,that will contain customerID's you've already fetched),but juat to add a new one-to-one elationship to your customer - latestDocument, and a inverse to it, and just make request to the documents,in which isLatestToCustomer is not nil.