Valyrian Steel vs. Valyrian Steel

Happy Monday. I thought it would be fun to discuss all of the times that we have seen valyrian steel (or equivalent) weapons clash.

Daemon I Blackfyre vs. Gwayne Corbray (196 AC)

During the First Blackfyre Rebellion, while The King Who Bore the Sword was in GOAT mode, Daemon I Blackfyre (w/Blackfyre) and Gwayne Corbray (Lady Forlorn) faced off:

Daemon was the Warrior himself that day. No man could stand before him. He broke Lord Arryn's van to pieces and slew the Knight of Ninestars and Wild Wyl Waynwood before coming up against Ser Gwayne Corbray of the Kingsguard. For near an hour they danced together on their horses, wheeling and circling and slashing as men died all around them. It's said that whenever Blackfyre and Lady Forlorn clashed, you could hear the sound for a league around. It was half a song and half a scream, they say. But when at last the Lady faltered, Blackfyre clove through Ser Gwayne's helm and left him blind and bleeding. Daemon dismounted to see that his fallen foe was not trampled, and commanded Redtusk to carry him back to the maesters in the rear.

If Daemon wasn't such a compassionate dude (heh) the First Blackfyre Rebellion might have gone differently.

Bloodraven vs. Bittersteel (196 AC)

Another event from the First Blackfyre Rebellion, after Daemon dropped the sword, Bittersteel and Bloodraven had their first duel:

"There was much and more afterward, I know. I saw a bit of it myself . . . the rebels running, Bittersteel turning the rout and leading his mad charge . . . his battle with Bloodraven, second only to the one Daemon fought with Gwayne Corbray . . . Prince Baelor's hammerblow against the rebel rear, the Dornishmen all screaming as they filled the air with spears . . . but at the end of the day, it made no matter. The war was done when Daemon died.

and:

This was followed by Bittersteel's mad charge, with Blackfyre in his hand, as he attempted to rally Daemon's forces. Meeting with Bloodraven in the midst of the charge, a mighty duel ensued, which left Bloodraven blinded in one eye and sent Bittersteel fleeing.

It should be noted that early version of this duel had Bittersteel losing a hand (in addition to the eye lost by Bloodraven).

Bloodraven vs. Bittersteel II (219AC)

It should be noted that Bloodraven/Bittersteel fought two (or more) duels (likely over Shiera Seastar).

The Second Blackfyre Rebellion proved a debacle, but that was not always to be the case. In 219 AC, Haegon Blackfyre and Bittersteel launched the Third Blackfyre Rebellion. Of the deeds done then, both good and ill—of the leadership of Maekar, the actions of Aerion Brightflame, the courage of Maekar's youngest son, and the second duel between Bloodraven and Bittersteel—we know well. -TWOIAF, The Targaryen Kings: Aerys I

and:

Daenerys Targaryen loved her captain, but that was the girl in her, not the queen. Prince Rhaegar loved his Lady Lyanna, and thousands died for it. Daemon Blackfyre loved the first Daenerys, and rose in rebellion when denied her. Bittersteel and Bloodraven both loved Shiera Seastar, and the Seven Kingdoms bled. -ADWD, The Kingbreaker

If interested: Dark Sister and Blackfyre: Could they meet again?

Daemon I Blackfyre vs. (Hypothetical)

Thanks u/significantmidnight7

When Prince Daemon had Blackfyre in his hand, there was not a man to equal him . . . not Ulrick Dayne with Dawn, no, nor even the Dragonknight with Dark Sister.

Arthur Dayne vs. Barristan (GRRM hypothetical)

While Dawn is not valyrian steel (it honestly has more in common with the blades or even bones of the Others than Valyrian steel) and the Daynes are more likely to be descendants of the First Men than have valyrian blood, I thought it was worth mentioning:

Who would win in a fight, Barristan Selmy or Arthur Dayne (in their best days)?

GRRM: Dayne... if he was armed with Dawn.

If both men had equivalent weaponry, it might be a toss-up. -SSM, The Sword of the Morning vs. Barristan the Bold, 3 Sept 2011

Im hoping to hear about Sandoq the Shadow using his valyrian arakh against a valyrian blade in Fire & Blood II.

TLDR: A list of times where a swordsman with a valyrian steel blade fought another with a blade of similar weaponry. Due to the sheer number of blades, converging plotlines and unfinished history I would expect to see a couple more of these pop up in TWOW/ADOS.