I was bored earlier and ran this exercise twice all by myself as I have all the character sheets here, and I had a hand in creating all but one of them so I'm pretty familiar with them all.

I rolled a D6 to determine which chromatic dragon we were fighting..... 6=red, 5=blue, 4=green, 3=black, 2=white, 1=reroll and it ended up being an adult green dragon.


The first combat started off 40ft apart with the dragon on the ground. I allowed prebuffs for the party so the Swashbuckler casted Bless(on Sorc, Fighter, and herself), the Sorcerer hasted the Fighter and Barb, and the Bard Enlarged the Barb and also used Inspiring Leader. When I rolled initiative for everybody and the dragon went last. The Swashbuckler did her Protector Aasimar transformation and dashed/flew away. My large Barb went next and ran up and successfully grappled the dragon sealing it's fate. The hasted/blessed Fighter ran up and hit the dragon with 5 out of 6 attacks with a +1 Longsword, the blessed Sorc hit it with 2 Firebolts, and the Bard Vicious Mocked it all before it could have a turn. It was reasonably successful with it Frightening Presence getting the Fighter, Bard, and Sorc and also hit those 3 with it's breath weapon. The only 2 in melee range were the fighter and barb which is it focused all it's attacks on. My Barb is hilariously resilient getting hit several times with claw attacks, but always taking half damage and no damage on one using Stone's Endurance. The Sorc hit hard with Booming Blade before flying away again. After 6 more attacks from the melee guys and a repeat of round 1 from the Bard and Sorc, it was already hurting bad by the end of round 2 and still couldn't move. It also didn't recharge it's breath weapon. On it's second turn, I debated about would it spend it's attack trying to break the grapple of attack and decided that there was a slightly higher chance of it attempting to break the grapple so I gave it a 60% of trying to break grapple and a 40% chance of just attacking more. I rolled a % die and ended up attacking more. This time the Swashbuckler failed the save to be frightened, but still hit with a light crossbow attack even with disadvantage, and after the 3 punches to the face from the Barb, it only had 20hp left. The fighter finished it off. Throughout combat it used all it's legendary actions attacking the Fighter and Barb.

I wiped the page clean and reran it, but this time the dragon had +49 more HP, and was 40ft away but also 40ft in the air, and when I rolled Int again, the dragon went before the Bard and Sorc. Party had same buffs as before.
The swashbuckler always goes first and did the same exact first round. This time the Barb couldn't reach the dragon so he used Chaos Bolt and hit for wimpy damage. The blessed/hasted fighter hit it with 6 straight longbow attacks. The dragon frightened everybody but the Rogue, and hit everybody but the Rogue and Barb with it's breath weapon. It also recharged it's breath weapon. It hit the Fighter with 2 claw attacks which dropped the Fighter to 0hp. The frightened Sorc dropped Fireball on it for decent damage and ran away. The Rogue hit it hard with Booming Blade and dashed away. 4d8+4d6+5+9. The frightened raging large Barb hit it 3 times with rocks for 1d4+1+5+2 damage each. The dragon was less successful with it's breath weapon this time as everybody had scattered but it did drop the Bard to 0hp. The Sorc hit it again with Fireball, and the Rogue hit it again with Booming Blade. The dragon essentially wasted it's 3rd turn attacking my Barb before retreating. The Blessed Sorc hit it with a Firebolt twice and the Rogue hit it a 3rd time with Booming Blade to start the 4th round and it was dead.


So yeah keeping it in the air, it lasted 1 extra round, but was still not that difficult. The first combat was over as soon as it rolled a low initiative and went last. It was especially over when it got grappled. I'd say the first combat was a good rounded group effort, but the second time around, the Aasimar Swashbuckler was the star of the show. Hitting it with 3 Booming Blades did a LOT of damage easily 2/3 of the total damage, and it managed to never be frightened or even be targeted with the breath weapon as it was off alone away from the group. It was the target of all Legendary Action attacks in the 2nd combat, but never even got below half HP. The Bard seemed to be the most useless, but did provide the party with +13 temp hit points as well as some Inspiration dice here and there for the Fighter or Rogue so I guess it was more useful than it seemed. A Hasted Fighter using it's Action Surge in the first round deals a lot of damage. Being Blessed allowed it to hit with almost every attack.

This was just a pure fight thing. No RP or anything of course. The dragon didn't have any reason to fight to the death, but that's not what this was about. I still want to do this properly and use an adult red next time.

I'm open to suggestions on what I could have and/or should have done differently.