Stephenson fought in battles during the war as well as playing a role in the prelude and aftermath of some of the fighting. At the June 18, 1832 Battle of Waddams Grove Stephenson led a dozen men against an unknown number of hostile Sauk. The battle, which descended into a hand-to-hand fight, resulted in three of Stephenson's men being killed. Stephenson was shot and severely wounded in the encounter. Though Waddams Grove did little to put an end to Sauk raids in the region, it did help bolster public confidence in the militia. Less than two weeks later, Stephenson was involved in the aftermath of the raid at Sinsinawa Mound, in present-day Grant County, Wisconsin. When news of the attack at Sinsinawa Mound reached Galena, Captain Stephenson set out with 30 soldiers to pursue the raiders. Once at Sinsinawa, they buried the "most shockingly mutilated" dead at the mound; both of the men killed, John Thompson and John Boxley, had been scalped, and Thompson's heart was missing. Stephenson followed the Sauk trail to the Mississippi River and stopped, the raiders having apparently crossed the river. Stephenson's party returned to Galena without finding the group responsible for the attack.