Van vs. the Dragon
Van's first fight happens on Earth before Hitomi has any idea who he is. The dragon appears on the school track, Van engages it with a sword and Hitomi's vision gives him the warning he needs to avoid a fatal strike. He kills the dragon and cuts the Drag-Energist from its body, completing the rite that will let him claim Fanelia's throne.
The Breakdown
Van has the courage and skill to finish the fight, but Hitomi changes the outcome before either understands what her visions mean. The reward is not treasure in the usual fantasy sense. The Energist becomes the key that awakens
Escaflowne in the next episode. The first battle therefore introduces Van, Hitomi's role in his survival and the power source of the series' central machine in one sequence.
Debut: Ep 001 - Fateful Confession
The Fall of Fanelia
SPOILER!
Van returns home expecting a coronation and instead watches Zaibach erase his kingdom. Invisible
Guymelefs strike before Fanelia can mount a normal defense. Van awakens
Escaflowne and fights back while Balgus tries to hold the attackers away from the young king and Hitomi. The battle ends with Fanelia burning, Balgus killed and Van forced out of his own country.
The Breakdown
This is less a duel than a demonstration of technological mismatch. Fanelia has strong warriors and a legendary Guymelef, but Zaibach controls when and where the defenders can even see the enemy. Van's first victory with Escaflowne cannot save the kingdom. The series makes that loss permanent enough that nearly every choice he makes afterward carries Fanelia inside it.
Van vs. Allen
Van's first real sword duel with Allen is exactly the fight the younger prince needs and absolutely does not want. Allen is an experienced Knight Caeli, trained by Balgus and comfortable enough with a blade to expose how much of Van's confidence still comes from anger and royal pride. Van attacks hard and loses.
The Breakdown
There is no hidden super move here. Allen has better timing, discipline and experience. That matters because Van has just survived a dragon, awakened
Escaflowne and lost Fanelia, all events that could convince him he is already ready for the war ahead. Allen proves otherwise in a few minutes. Their rivalry later becomes tangled with Hitomi, but the first fight is fundamentally a lesson from one swordsman to another.