[Hank 91]

The conventional wisdom in these situations -- admittedly, conventional wisdom is not always best -- is to schedule your timeouts backwards. If you've got only one, use it after third down. Two? After second and third. The idea is that if you give up a first down, it doesn't matter. And if you can force a team into third and long and they're foolish enough to pass and risk a clock-stopping incompletion, all the better. You've got a timeout left for your offense.

[Hank 91]

The conventional wisdom in these situations -- admittedly, conventional wisdom is not always best -- is to schedule your timeouts backwards. If you've got only one, use it after third down. Two? After second and third. The idea is that if you give up a first down, it doesn't matter. And if you can force a team into third and long and they're foolish enough to pass and risk a clock-stopping incompletion, all the better. You've got a timeout left for your offense.