A painting capturing the momentous victory in battle of Indian rulers over British East India Company troops in 1780 is up for auction in London.
Bids at Sotheby's sale on Wednesday will start at £370,000 ($485,000).
Tipu, known as the "Tiger of Mysore", became the Company's fiercest foe until he was defeated and killed in 1799.
Historian William Dalrymple has described the painting of what unfolded in Pollilur as "arguably the greatest Indian picture of the defeat of colonialism that survives".
Mr Dalrymple, whose book, The Anarchy, documents the rise of the East India Company in the 18th Century, has called it "the most crushing defeat" and one that "nearly ended British rule in India".
Tipu, who got his first command at Pollilur, "turned the tide" against the British, Mr Dalrymple told the BBC.
Scenes from the battle were first commissioned by Tipu himself in 1784. They were painted on the walls and frescoes of his palace - Daria Daulat Bagh - in Srirangapatnam, then the capital of Mysore in southern India.
One of those paintings was sold at auction in 2010 and acquired by the Museum of Islamic Art in Qatar. It was brought to England by Colonel John William Freese, who was in Srirangapatnam after Tipu's defeat. His family handed it down over generations before selling it in 1978 to a private collector, who sold it in 2010.
The origin of the second painting, which Sotheby's is now auctioning, is less clear. Given how similar it is to the one acquired by Freese, it's assumed to have also been brought to England by a British officer.
It first appeared at auction in the early 1980s, Benedict Carter of Sotheby's told the BBC. "But we don't know what happened to it in the 100 years before that." It has only been briefly displayed before, in 1990 and 1999, leaving it in a "pretty remarkable state", he said.
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The painting depicts - in vivid, triumphant and gory detail - what happened on the morning of 7 September 1780.
Tipu ambushed Company forces led by Colonel William Bailie near a village named Pollilur not far from Madras (now Chennai), a major British trading outpost at the time. By the time Haider Ali arrived with reinforcements, the "work had been pretty much done", Mr Dalrymple says.
The 32ft long painting, which stretches across 10 sheets of paper, shows Tipu atop an elephant while overseeing his troops. Towards the other end of the painting, his cavalry is attacking Company forces on both sides as they form a square around an injured Bailie, who is in a palanquin.
It even shows a cart of ammunition exploding - a moment in the battle, Mr Dalrymple writes in an essay accompanying the auction - that was recorded by Bailie's younger brother John: "Two ammunition tumbrils were hit and both blew up simultaneously, making 'large openings in both lines, on which their Cavalry made the first impression. They were followed by the Elephants, which completed our overthrow."
"It's a stunning masterpiece, it's unprecedented," Mr Dalrymple told the BBC
He believes that's why despite the spectacular defeat, the paintings were commissioned by British officers such as Col Freese - because the murals in Srirangapatam were just as, if not more, striking.
Another theory is that the two paintings were made as preparatory drawings when the Company restored the frescoes in Serirangapatnam under the orders of Arthur Wellesley, the future Duke of Wellington. Tipu himself had ordered the murals whitewashed after losing a subsequent war to the Company - the images were "incredibly bloody", Mr Dalrymple says, and having them painted over was perhaps a gesture of peace.
Despite his eventual defeat, Tipu was respected by the British for his military acumen and "the way he died gallantly in battle", according to Mr Dalrymple.
So it's not so surprising to historians that the British chose to retain evidence of the Battle of Pollilur.
The painting's significance is drawn from the battle's import, Mr Dalrymple says. Tipu was "the most feared by the British", the only Indian ruler at the time who never allied with them.
By the mid-18th Century, the Company gained an advantage on the battlefield in India, thanks to military innovations in Europe. But Tipu, Mr Dalrymple says, managed to match them by 1780, as the win in Pollilur shows.
In Pollilur, Tipu's army had better guns, better artillery and his cavalry was better prepared in terms of inventions and tactics. They were able to fire rockets from their camels, for instance, and this was a technique, which, in turn, later inspired the British to invent their own rocket system.
But in the end, despite Tipu's continued resistance to the English, there was no lasting alliance among the Indian kingdoms that had emerged from a splintered Mughal empire.
Now, with his legacy as a Muslim king being re-evaluated in an increasingly Hindu nationalist India, the Battle of Pollilur is a reminder of the obstacle he posed to British conquest.
So much so that when he was killed, the victors took his campaign tent back to Britain, where it remains to this day - a trophy from the defeat of the "Tiger of Mysore".