The next fight is a challenging one. The dragons are back! A young brass dragon and a half-dragon. Zumfir hears that fire won't be effective and the dragon will fly but there will be a magical roof 60ft up that will limit how far away the dragon will be. 

When news breaks about the upcoming challenge, Gimmond appeared a touch frazzled by it. "If that half-dragon intends to ride the young brass as a mount, things will get tricky. I will endeavor to try and demount him if such becomes the case, but beyond that my friends, I suggest we do not keep to prior formations for this one. For if both are swift enough and capable of unleashing breath weapons, our time in the arena may soon come to a swift end!" The last part is said with a bit of mirth to his voice, but the expression he held after conveyed seriousness, suggesting not all had been made in jest. 

Zumfir hums, closing his eyes as he tries to think of the best approach against the dragon. "We need to get rid of the dragon as soon as possible. I can make one of you protected against flames, and i can issue a command to force the dragon to drop on the ground."

"And just like Gimmond said, we should not stay too close to each other, else we will be fried by the dragon's breath."

"Those are some good ideas, Gimmond and Zumfir.  We'll be sure to spread out and try to ground the dragon as soon as we can."

Twinkle nods. "I can try to get up to the beast if it flies low enough. I agree with everyone that we should spread out."

The monk will activate her ring of jumping in advance if possible.

Gimmon runs a hand through his beard thoughtfully, then shook his head. "Much as I'd like to take whatever protection you might extend Zumfir, I think it'a be better for you to save it for yourself. Because if either of our next opponent has any sense about them, you'll quickly become their prime target." He'd say. "Otherwise, it seems we're in agreement. I'll take the south entrance, and Athos you take the north. And so on and so forth."

Just before the match, Gimmond would of course activate his winged boots in anticipation of the fight ahead of the group.

I've given extra irl time for discussion this time as it should be an extra challenge compared to recent ones. Possibly too hard a challenge but the last few fights have all been a couple of CR above your level. This one is two slightly lower CR but that obviously doesn't fully balance out. It sounds like you are more or less in agreement, so I will start the fight probably in the morning just so you can iron out details (such as who gets protection) and any finer plan points you might want to discuss 

Zumfir hums in aknowledgement. He casts Protection from Energy on himself, protecting against FIRE damage.

[Depending on how far apart we are allowed to enter the arena, I'd suggest at least 15 feet apart, 30 if possible.]

"I've seen a dragons' breath wipe out entire hunting parties that were careless enough to stand close together."

[Swiftgale, to clear up two things that may come up during the fight in advance:
- How easy are the walls of the arena to climb? Do they require a check, or are they difficult terrain? [Climb rules reference link]
- Would you allow chaining of a jump and a teleport at the jump apex? Specifically the jump spell and the goliaths Cloud Giant Ancestry (which Twinkle is) [Goliath reference link].]

The walls of the arena are not climbable. They are effectively magical barriers of force to protect the spectators.

I would allow the jump and teleport as the jump is movement (as long as the spell was cast on a previous turn) and you time your bonus action within your movement. Just don't forget fall damage 

[Good with me, thanks!]

The crowd are restless for this large fight.

The dragon flies straight up from the centre of the arena, 60ft up (about 25ft along in plan from each of you. So 65ft away when considering diagonal). The half dragon enters through the southern entrance (so next to Gimmond). 

I've assumed you are each adjacent to a gate. Athos is north, Twinkle is east, Gimmond is south, Zumfir is west. Any changes let me know.

Initiative wise, Twinkle, Athos and Gimmond are up, then the dragons, and then everyone in any order going forward.

Might be able to do a map update tomorrow 

Athos will see the half-dragon next to Gimmond and launch a level 1 guiding bolt at it.  26 to hit for 9 radiant damage and the next attack against the half-dragon has advantage.

Gimmond grins and seizes the opportunity, lasting a nasty spear thrust where the bolt had landed, before shifting stance and weaving his way into a follow-up strike in another weak point between whatever served as armor for the Half-Dragon. Each time he called out tactical advise to further encourage his allies to move, but ultimately leaving such to their discretion. Then in a bold maneuver, he took flight, opening himself up to to attack. But short of being driven back into the earth by any such retaliation, the dwarf remained steadfast and double-timed it up to fly side by side with the dragon poised to strike it down from the sky.

Ac: Attack Half Dragon with a most vicious spear!
Attack #1: One-Handed Vicious Spear vs Half Dragon(AC ??) - To Hit: 27(Nat 20!) For: 32 Piercing Damage. 
(Spent Superiority Die for Maneuvering Attack, damage included in above. Athos can, if he so chooses, reaction to move at half speed. Target is also sapped*) 
Attack #2: One-Handed Vicious Spear vs  Half Dragon(AC ??) - To Hit: 25 For: 22 Piercing Damage.
(Spent Superiority Die for Maneuvering Attack, damage included in above and Twinkle can, if she chooses,  spend reaction to move at half speed.(Reapplying sap mastery if needed))

Mo: Using full 30ft to closer Brass Dragon, provoking AoO from Half-Dragon.

IF AoO hits and does not impede movement:
Ba: Second Wind, regaining 11 Hp. And using tactical shift to fly an additional 15 ft towards dragon without provoking further AoOs (if somehow possible) 

Action Surge: Dash fly into melee with dragon, flying parallel to the south of it.

IF Aoo does NOT hit.

Action Surge: Dash fly into melee with dragon, flying parallel to the south of it regardless.

Ba: Attack Dragon with Pole Strike! (if within reach of dragon. Otherwise, still burning second wind for Tactical shift's extra movement)
Attack #3: One-Handed Vicious Spear vs  Half Dragon(AC ??) - To Hit: 20 For: 15 Bludgeoning Damage.

Sap: If you hit a creature with a Spear, that creature has Disadvantage on its next attack roll before the start of your next turn. (Note: Always applying/reapplying as needed)
Tactical Shift: Whenever you activate your Second Wind with a Bonus Action, you can move up to half your Speed without provoking Opportunity Attacks.

 

@Swift: Not sure if read group message, but is using a mount allowed in the arena? This won't matter for this current match, but would've affect prior feat choice/build choices going forward.  Because I took mounted combatant initially.  

Athos will move south 15ft thanks to Gimmond's ability.

(Map will come tomorrow. Twinkle is still up)

Gimmond did you roll double dice for the manoeuvre on the crit? And the AoO misses. I thought I replied to say mounted was fine. I might never have sent the reply though. Despite me saying the dragon was 65ft away, I didn't take into account its size and the fact it takes up multiple squares. So with 60ft of movement you can reach it with the dash and then BA attack.

To Swift: I did indeed for.. not the greatest rolls. And unless they've changed how crits work for 2024 that I missed, I believed that like sneak attack and smite it would still get doubled from a crit since no save throws were involved. If I'm mistaken again because of crit changes, go with the '1' from that damage segment. Also, that BA attack's dice was rolled twice with savage attack origin feat, which I neglected to mention in my post. 

I haven't checked tbh, I assumed they would be doubled and I was making sure you had doubled them as I didn't want you missing out. It's easy to miss that when the dice roller doubles the main damage automatically but the manoeuvres are separate 

Seeing that Gimmond was well poised to do something about their flying foe, Twinkle rushed over to the half dragon, determined to take out at least part of their opposition. On her way there, she infused her limbs with elemental energy.

From a distance of 15 feet, the monk unleashed a barrage of punches against the half dragon. 

Action:
Attack 1: 17 damage: 9 force + Stunning Strike (Con Save DC 14: Failure: Stunned until start of Twinkles next turn, Success: his speed is halved until the start of Twinkles next turn and next attack against him before then has advantage. So in either case, Twinkles second attack has advantage. If the attack doesn't hit, Twinkle will instead try to stun on her third attack.)
Attack 2: 11/17, damage: 14 force

Bonus Action [Unarmed Strike]:  
Attack 3: 28/21, damage: 8 force

Map (Dragon and Gimmond up 60ft higher)

 Athos hits the half dragon, leading the way for Gimmond to get some powerful hits before he reaches the dragon and gets a solid hit there too.

Twinkle just misses on her first two hits. But the third one hits. And a Nat 1 save so the half dragon is stunned.

The dragon looks around and moves 5ft west and up (still in melee with Gimmond) and it breathes out fire in a 40ft line, catching both Gimmond and Twinkle. Both need to make a DC14 dex save. 30 fire damage on a fail, half on success.

Everyone is up! Half dragon is stunned for Zumfir, Gimmond and Athos's actions regardless of when Twinkle posts.