A fitting epic end to the battle. Between all the attacks, the dragon is left on 2hp.

But it also rolled a 16 on its save against command, so on its turn, it has to drop prone and end it's turn. 

Before any of you can have your next turn however, the dragon was flying. Becoming prone causes you to fall. The dragon was 60ft up so the damage from the fall is greater than it's 2hp, and the resulting thud brings the combat to an end!

While celebrating, you each get 500gp and a level up 

Athos will stand against the blast of air as the dragon hits the ground; then put a foot on it and give his customary cheer of victory to the crowd.  "Good job going toe to claw with that dragon Gimmond.  Sorry I couldn't help as much with it in the air.  What an amazing celestial you summoned Zumfir.   That was amazing that you managed to stun the dragon from the air Twinkle."

Twinkle steps back just far enough to not get involved in the dragons sudden and bone-cracking encounter with the ground. Grinning, she turns to her companions and waves at the crowd. 

"Well done friends! I didn't know you could look so graceful in the air, Gimmond. And thanks for the healing Athos."

The monk then busies herself with picking up all of the daggers she's thrown, yanking one free from the dragons head.

Gimmond lands not to long after the dragon. Although Zumfir had done a great job in mending his injuries, he was still covered in plenty of blood and moved with a degree of stiffness. Yet nevertheless, he wore a grin as he joined the others in celebrating the party's success! "Ah, no worries there Lad! We dwarves are made of sterner stuff than most might give us credit! And you -- all of you did more than enough back there! Now if you'll excuse me, I gotta see a man about a horse and some barding!" He declared, and soon made his way out of the arena, picking up his prize on the way out.

OOC: Officially Buying Warhorse using 500gp Voucher, and spending 800 gp to equip it with Splint Armor Barding. 

Perception: 8. 

Insight: 15

Athos will follow Gimmond. "I'm excited to see you ride a horse into battle.  What are you going to name it?"

Zumfir sighs, "This has been a hard battle. i wonder what will be the next one . . . worse than a dragon?" 

Perception: 28 (nat 20)

Twinkle stashes her gold and is too busy studying the training exercises manual to pay much attention to anything. (Foregoing a check, the others got this)

What could be worse than a dragon indeed. Maybe  larger dragon. Or a hybrid... Or two dragons. Or a combination of the lot! You hear the next fight is two chimera. Better watch out for their cone fire breath. 

"Two chimeras?  This should be fun."  Athos readies himself for the next round.

"Oof, yeah, uhh, probably not good to bring in horses versus fliers. Especially the sort that can, well.. breath fire too!" Gimmond snortles at first. But then, he turns his head and began stroking his beard. "Although, if I could maybe hire a wizard to make'm fly... No! Nonono, it's just not done!" He had to admit to himself, before with a sigh, he got ready to prepare himself again. "I'll try to the one busy best I can, but the rest of you focus on the other one. Once it's down we can double take care of the last one, yeah?"

Twinkle thinks for a moment. "If these things stay out of reach of my daggers, they'll be quite a nuisance. Perhaps I can find a way to bring the fight to them." 

The monk rummages in her backpack and produces a grappling hook. "We used those back in the spine to get around." She wonders, perhaps she could catch creatures too.

[Swiftgale, how would you rule if Twinkle were to try and throw a grappling hook + rope at enemies? Possible or no? Her main goal would be to either pull them down if they are same size or smaller than her, or climb up if they're larger.]

Zumfir hums, scratching his chin. "Maybe . . . if i'm successfull on what i will try to do, we will just need to fight one at a time. Again, hopefully i can manage to do that. Either way, i shall do the same as before, focus on staying back and healing." 

There are no rules for grappling hook on an enemy. But I like the idea of it. I will rule it as follows:

You do the action as stated on the item with the same dc. On a success, the creature gets a save as if you took the unarmed attack grapple option (with your unarmed grapple dc). On a successful grapple, I will allow you to use your movement to either pull them down or you up. Same as ordinary grapple moving, the moving person moves 1ft for every 2ft movement. If on their turn, they break the grapple and you are climbing up, you will fall and take falling damage. Same if they die. I will also say that if you are climbing up to them, you have disadvantage on attacks as you are trying to attack while holding on with one hand, and possibly being bucked around while in the air (effectively trying to attack while also doing rodeo 50ft up) 

[That sounds fair to me!]

Twinkle nods to Zumfir. "That sounds better than me getting bashed against the arena walls. But if worst comes to worst, I'll try my alternative." With that, the monk attaches her rope to to the grappling hook and straps the whole thing to her belt to have it ready when needed.

The battle starts, and the chimeras burst out, 10ft in the air currently. You are all up. 

"Alright! Remember the plan. I'll take care of the one in the north, while you lot deal with the other one. Soon as its down, back me up." Gimmond doesn't wait to see how his reminder is taken before racing forward and leaping into the air; his winged boots already primed and ready to hold him aloft as he races through the air to confront one of the chimeras. "Let's see what you're made of you oversized badger!" He cries out, goading the creature with the first two strikes of the spear, before bringing the back end around for a vicious swipe across one of its head, dazing it long enough to potentially fall to the ground!

... That is, had he not needed the extra burst of speed to rush the creature in the first place.

Mo: If possible, using full movement to get within 5ft of chimera. Gimmond will position to be within 5ft of it, but hovering only 5ft off the ground since it only flew up 10ft.
Ba: If unable to get within melee with just 30ft of movement, burning a use of Second Wind for Tactical Shift to move an additional 15ft.

Ac: Attack Chimera(#1) with a most vicious spear!
Attack #1:  One-Handed Vicious Spear vs Chimera #1(AC ??) - To Hit: 12 For: - Piercing Damage. 
Attack #2:  One-Handed Vicious Spear vs Chimera #1(AC ??) - To Hit: 21 For: 18 Piercing Damage. 
If hit, using Goading Attack on target. Wis Save(DC 15) or have disadvantage on all attacks not on Gimmond. 
Also sapping target, causing 1st attack from it to be at disadvantage.

Ba: If not spent for tactical shift, Polearm Strike with a most vicious spear!
Attack #3:  One-Handed Vicious Spear vs Chimera #1(AC ??) - To Hit: 21 For: 19 Bludgeoning Damage. 
If hit, using Trip Attack on target. STR Save(DC 15) or fall prone. And since 10 ft in the air, it'll likely take an add d6 of fall damage.

Note: Bonus damage from maneuvers included in overall damage.

(OOC: So, after further research into my origin feat, I'm not longer sure if Savage Attacker works also grants its 2ndry roll to the damage for weapons like vicious weapon, flaming weapon, etc. So for now, I'll just strictly stick to only rolling twice for the weapons basic damage dice. So for that 2nd attack, ignore the extra 3d6 in the roller thing.)

"On it, Gimmond."  Athos will move towards the southern chimera and cast command on it "Grovel".

Zumfir raises his hand, turning towards the chimera on the north. "Wait arthos, let me try something!" He stated before his friend could cast the spell; Then, with a movement of his hands, he whispers an incantation, casting Banishment Upon the chimera.

17 CHA Saving throw or be Banished for 1 minute

Athos will redirect his command for the other chimera if Zumfir's banishment succeeds.  WIS 17 on the save.

Twinkle attacks the chimera that Zumfir has targeted with his banishment spell. If it gets banished, Twinkle instead rushes over to Gimmond's chimera. 

The monk activates her elemental attunement to give herself enough reach to attack the chimeras from the ground. She then pummels the target with multiple attacks, also attempting to stun it. If any chimera she targeted is prone, she moves within 5 feet of it to get advantage on her strikes and then stays there. 

[If the Twinkle has advantage, take the higher number, otherwise take the first.]

Action:
Attack 1: 18/22 damage: 7 force + Stunning Strike (Con Save DC 14: Failure: Stunned until start of Twinkles next turn, Success: chimeras speed is halved until the start of Twinkles next turn and next attack against it before then has advantage.)
Attack 2: 26/19, damage: 14 force

Bonus Action [Flurry of Blows]:  
Attack 3: 20/25, damage: 8 force
Attack 4: 17/14, damage: 11 force