You can acheive this by making the two tracks "part of a compilation." Go to iTunes, select 'Get Info" on the tracks, in the 'Info' tab, tick the checkbox at the bottom-right corner that says 'part of a compilation.'
Thanks for the suggestion. I just tried that but as soon as "Loadout" finished, it went to a random song instead of going to "Stay". Both songs are checked as part of a compilation. Any other thoughts?