As the army swung around the Confederate right flank in the direction of Spotsylvania Court House, Sheridan's troopers failed to clear the road from the Wilderness, losing engagements along the Plank Road on May 5 and Todd's Tavern on May 6 through May 8, allowing the Confederates to seize the critical crossroads before the Union infantry could arrive.
Da hæren svingede rundt om sydstatshærens højre flanke i retning af Spotsylvania, havde Sheridans tropper ikke held til at rydde vejen fra the Wildernes og tabte træfninger langs Plant Road 5. maj og Todd's Tavern mellem 6. og 8. maj, hvilket tillod sydstatshæren at nå nogle kritiske vejkryds, inden Unionens infanteri kunne nå frem.