A shekara ta 1608 Crawford ya jagoranci rundunar sojojin Scotland a Strabane da Lifford wadanda suka bi Sir Cahir O'Doherty
Burning of Derry, ya taimaka wajen kayar da abin da aka sani da O'Doherty's Rebellion. Don hidimarsa, an ba shi kadada 1,000 na ƙasa kusa da Kilmacrennan a cikin County Donegal, wanda ya cancanci zama mai hidima. Akwai wasu ƙiyayya na ƙasar da aka ba Crawford da wani Scot William Stewart a gaban tsoffin sojojin Ingila da na Irish na Yaƙin Shekaru Goma, amma sun sami goyon bayan James I.