Bleeding Oak was so named for the horrifying loss Blackmarsh suffered against the Menethil forces during the War of Acquisition. Lord Holden's decision to stage his final battle here is one considered questionable in military terms, though fitting symbolically.
Bleeding Oak was a hilled section of the forest with several creeks running through it. After disengaging from Sir Geoffrey's forces, Lord Pendleton intended to take his veterans south and then cut northward to strike the Menethil army in a final push to seal them out of Blackmarsh. Bleeding Oak was also the swiftest means by which Sir Ulric could have made his way to Ebonloch Hold.
Extremely wearied by this point and outnumbered, Sir Ulric's men were initially pushed back nearly to the brink of collapse by Lord Holden's rested soldiers. By midday, Sir Ulric had lost a quarter of the men he had arrived with, and still had nearly half as many injured.
But Sir Ulric held firm, and after taking a horse, rode to meet Lord Holden in battle. The two crossed paths seven times, in which Lord Holden was nearly unhorsed. Upon seeing the potential shift in battle, Cedric Graves attempted to defect to Ulric's side, but was cut down. Shortly thereafter, a mass desertion effort began.
Lord Holden, abandoned, was forced to surrender.
Nearly all the lesser nobles that deserted were severely punished by Sir Ulric, though Dedrick later revoked their punishments in favor of gaining their fealty. In addition, had Sir Ulric not gained Lord Holden's surrender then, it is likely he would have been killed when Menethil forces converged upon their location.