The primary combatant groups were the Kiks.ádi ("Ones of Kíks", Frog/Raven) clan of Sheetʼká Xʼáatʼi (Baranof Island) of the Tlingit nation, and agents of the Russian-American Company assisted by the Imperial Russian Navy.

Members of the Kiks.ádi of the indigenous Tlingit people had occupied portions of the Alaska Panhandle, including Sheetʼká Xʼáat'i (present-day Baranof Island), for some 11,000 years.

[1][better source needed] Alexandr Baranov (Chief Manager of the Russian-American Company) first visited the island aboard the Ekaterina in 1795 while searching for new sea otter hunting grounds.

On 7 July 1799, Baranov, with 100 fellow Russians, sailed into Sitka Sound aboard the galley Olga, the brig Ekaterina, the packet boat Orel; and a fleet of some 550 baidarkas,[2]: 25–26  carrying 700 Aleuts and 300 other natives.

[3]: 175–176 Wishing to avoid a confrontation with the Kiks.ádi, the group passed by the strategic hilltop encampment where the Tlingit had established Noow Tlein ("Big Fort") and made landfall at their second-choice building site, some 7 miles (11 kilometers) north of the colony.

The Kiks.ádi objected to the Russian traders' custom of taking native women as their wives, and were constantly taunted by other Tlingit clans who looked upon the "Sitkas" as the outsiders' kalga, or slaves.

Led by Skautlelt (Shḵ'awulyéil) and Kotleian, the raiding party massacred many, looted the sea otter pelts, and burned the settlement, including a ship under construction.

[2]: 37–39 Following the Kiks.ádi victory, Tlingit Shaman Stoonook, confident that the Russians would soon return, and in force, urged the clan to construct a new fortification that was capable of withstanding cannon fire, and provided an ample water supply.

The Tlingit merely hoped to stall the Russians long enough to allow the natives to abandon their winter village and occupy the "sapling fort" without the enemy fleet taking notice.

However, when the Kiks.ádi sent a small, armed party to retrieve their gunpowder reserves from an island in nearby Shaaseiyi Aan (Jamestown Bay), the group (electing not to wait for the cover of darkness, instead returning in broad daylight) was spotted and engaged in brief a firefight with the Russians.

When the smoke cleared, it was evident that none of the expedition, comprising upper-caste young men from each house (all future Clan leaders) and a highly respected elder, survived the encounter.

[9]: 157–158 The Kiks.ádi warriors, led by their new War Chief Ḵʼalyaan (Katlian) — wearing a Raven mask and armed with a blacksmith's hammer, surged out of Shis'kí Noow and engaged the attacking force in hand-to-hand combat; a second wave of Tlingit emerged from the adjacent woods in a "pincer" maneuver.

The Tlingit's goal had been to hold out long enough to allow the northern clans to arrive and reinforce their numbers, but the shortage of gunpowder limited their ability to remain under siege, a factor that made ultimate victory seem less likely.

[7] The Tlingit concluded that a change in tactics was in order: rather than suffer the ignominy of defeat on the battlefield, they formulated a strategy wherein the Clan would disappear into the surrounding forest (where they felt that the Russians could not engage them) and establish a new settlement on the northern part of the island.

[9]: 161–162 On 8 October, Captain Lisianski visited the abandoned Tlingit fortification, in which he estimated eight hundred males lived, and recorded: The fort was razed to preclude the possibility of its being used as a stronghold against the Russians and their allies ever again.

[10] The first leg of the Tlingit's sojourn entailed a hike west from Gajaa Héen to Daxéit (the Clan's fishing camp at Nakwasina Sound, where each May the Kiks.ádi harvested herring eggs, a traditional native food).

From there, the group's exact path across the mountains north to Cháatl Ḵáa Noow (the Kiks.ádi "Halibut Man Fort" at Point Craven in the Peril Strait) is a matter of some conjecture.

Several warriors remained in the vicinity of Noow Tlein after the Battle as a sort of rear guard, in order to both harass the Russian settlers and to prevent them from pursuing the Kiks.ádi during their flight north.

In November, 1805, Cháatl Ḵáa Noow was visited by John DeWolf and Georg von Langsdorff from Sitka, with several Alutiiq men and the daughter of a Tlingit clan head to serve as translator, provided by Baranov.

[13] Atop the kekoor (hill) at Noow Tlein, the Russians constructed a fortress (krepostʼ) of their own, consisting of a high wooden palisade with three watchtowers (armed with 32 cannons) for defense against Tlingit attacks.

In September 2004, in observance of the Battle's bicentennial, descendants of the combatants from both sides joined in a traditional Tlingit "Cry Ceremony" to formally mourn their lost ancestors.