Route 66 (famous dead Murican hiway) - it Should be a 'rooter'.

router - yep, a thingie for making woodchips of a perfectly nice piece of wood.

rout - what happened to US in Vietnam (though we killed a Lot more of them while we were being ousted)

Arrgggghhh - then we have bow (both ways), bough, boffing (swords)

Gotta find the link I have somewhere, allegedly a kinda final exam for wannabe diplomats: a one-page compilation of all the above type homonyms and idioms and the other stuff that drives English-as-a-Second Language folks batty. Then the spelling.. NIFE as knife !?!
But NITE as night | knight