As with most cheeses the ideal pairing for cheddar depends how mature it is. A mild to medium block cheddar is going to be a lot easier to match (and in most cheeselovers’ eyes a lot less interesting) than a tangy cloth-bound cheddar of 18 months or more.
I know Thanksgiving has past but I came across such a good pairing for pecan pie at a friend's* house the other day I had to tell you about it. Her pie by the way was quite distinctive with a thin layer of soft caramel in the centre (and, obviously, crisp pecans on the top).
Pork and apple is, of course, a match made in heaven but the pairing was taken to new heights for me by mixologist Jack Adair Bevan of The Ethicurean who invented an Old Fashioned cocktail with a twist to go with a dish of slow roast pork.
I suppose I shouldn’t say this coming from the West Country but I often forget about cider when I’m thinking about cheese pairings. Not that I don’t enjoy it but there always seem more complex drinks with a wider range of flavours to experiment with.