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Before setting off to meet the Triballians, Alexander sent his war ships from Byzantium via the Black Sea into the Danube and ordered them to sail upriver and hold their position at a pre-designated location.

In the spring of 335 BC, Alexander marched his army northward until he found the Thracians. The Thracians had occupied the Shipka Pass and had secured their position atop a hill behind a fort made of wagons. Perched on top of this hill they waited until Alexander's army attempted the climb. Before they reached the top the Thracians released a barrage of wagons hoping to run the Macedonians down. Alexander, however, anticipated their plan and ordered his men at the top to form columns with alleys for the wagons to hurtle down and the men further down the hill to lie down in close formation with their shields over their heads.

As the wagons hurtled downhill, they were guided into the alleys by the formation and as they gained momentum, the wagons rode over a roof of shields without doing any damage to the men. With superb discipline exercised, not a single man was lost.

Alexander stormed the Shipka Pass and descended upon the northern plains in pursuit of the Triballian king who sought refuge on an island in the Danube. The Triballian army, which withdrew southwards, suffered an annihilating defeat.