Before we start, how do you position yourselves this time? 

Athos has been lucky with starting in the same spot each time.  Unless the others want a change up, he'll stay the same.

Twinkle will take up her usual position.

Gimmond will stick to the usual position as well in -- Wait! NO! We're fighting a dragon, so he'll start where the southern wolves did and shield equipped, but a free hand open at the start. 

Since they are fighting a dragon, Zumfir will stay a bit far from the group, being mindful of the breath weapon. He would be in the upper left corner of the arena.

The gate in the middle opens and a small (medium sized) dragon emerges. It sets off immediately, flying along the blue line shown, letting off a breath of lightning (a line) that catches Athos and Twinkle, and skims past Zumfir, just narrowly missing him.

Athos and Twinkle need to make a DC12 dex save or take 24 lightning damage. Halved on a success.

And everyone is up.

"Bout what I figured." Mumbled Gimmond as he watched two of his fellow get fried up by the dragon. His gaze then darts over to the dragon, and after taking but a moment to pat his chest and raise his spirits, he broke out into a charge with war pick in hand, readily digging his weapon into draconic hide! At one point as it is dug deep enough, Gimmond yanked as hard as he could to try and disrupt and distract the dragon, if but for a moment. "Athos! Now!" He barked out as well.

Mo: Using 25ft to get in melee, positioning to the south-east of the dragon.
Ac: One-Handed Warpick vs Dragon(AC ??) - To Hit: 14 For: 7 Piercing Damage. 
Action Surge - Ac: One-Handed Warpick vs Dragon(AC ??) - To Hit: 21 For: 7 Piercing Damage.
On first attack to hit, using maneuver attack to deal an additional 4 piercing damage and allowing Athos to spend reaction to move half his speed before taking his turn.
If hit, target is also Sapped, rendering its next attack roll at disadvantage.

Sap. If you hit a creature with a War Pick, that creature has Disadvantage on its next attack roll before the start of your next turn..

 

(OOC: Legit forgot we weren't level 5 yet, so burned action surge to attack again)

(Also, if dragon is meant to have ended its turn airborne and out of reach of melee, Gimmond will throw his javelin instead. So, same attack rolls and movement, but will roll damage for javelin instead shortly)

Athos will use his reaction to move up thanks to Gimmond.  On his turn, he'll move up the remaining distance.

He rolled a 16 on his dex save, taking 12 lightning damage.

If the dragon is within melee, and not out of reach airborne he'll attack with his longsword:

Still a little tingly from the lightning breath he gets a 13 to hit, for 12 slashing damage.

The dragon is not out of reach airborne. Up close you do see that the DM isn't being too mean to melee characters yet there seems to be runes on the dragons wings that glow faintly every time the dragons altitude looks to be increasing.

Only the action surge hit out of Gimmond and Athos. (14<AC<=21)

Zumfir casts Blindness/Deafness on the dragon, DC 14 CON or be Blinded for 1 minute

Twinkle was preoccupied with waving at the crowd, so the sudden emergence of the dragon catches her unawares and she is hit by the full brunt of its breath. (Dex Save: Nat 1 for a total of 7). The crackling energies surge through the monks body, almost knocking her out cold.
[If Twinkle wasn't Though, this would have been it! 😅]

She keeps her footing, staggering for a moment, then rushing towards the dragon. On her way there, her fists and feet burst into flames, as she channels elemental energies.
The monk maintains a 10 foot distance from the dragon, bombarding it with fire (thanks to 15 foot reach) and then retreats to behind a cage.

[Action]
Attack 1: 12 , damage: 7 fire
[Bonus action] Flurry of blows
Attack 2: Nat 20, damage: 13 fire
Attack 3: Nat 1

[In this post: The duality of dice]

The dragon barely passes its save (15) so is not blinded.

Twinkle gets one hit on the dragon, dealing a good chunk of damage. 

(I do not have time to update the map. But the dragon isn't moving) The dragon swipes out with its claws. One against Gimmond and one against Athos. But both missed with single digit attack rolls.

You are all up again

Athos charges his blade with a holy smite and attacks back at the dragon with a 21 to hit , for 13 slashing damage and 5 radiant damage.

Zumfir will run towards twinkle, upcasting Cure wounds 2nd level.
 
Healing: 21, +4 from disciple of life equals 25 Healing.

Then, he will return to the backlines.

Gimmond wastes no further time in once again working the war pick into motion as he sought to tear into the dragon's flank the moment it was distracted by Athos. 

Mo: Using 25ft to get in melee, positioning to the south-east of the dragon.
Ac: One-Handed Warpick vs Dragon(AC ??) - To Hit: 23 For: 11 Piercing Damage and Sap vs dragon once more. 

Twinkle left. And the dragon is injured now (<50% health)

Twinkle perks back up after Zumfir all but blasts her with healing power. She whoops a "Thanks!" and then she's off, rushing towards the dragon. 

As before, the monk keeps a 10 foot distance to the foe, throwing flaming strikes at it past Gimmond and Athos.

[Action]
Attack 1: 17 , damage: 5 fire
[Bonus action] Flurry of blows
Attack 2: 24 damage: 7 fire
Attack 3: 9

She then retreats far enough to be out of range of the dragons dangerous breath if it wanted to catch her and one of the other melee combatants together.

The first attack just barely hits, for a total of 12 damage. The dragon is unlikely to get another turn.

Its breath weapon does not recharge, so it takes another two swipes, one at Athos and Gimmond.

A 12 to hit Athos, and a crit on Gimmond for 15 slashing damage and 11 lightning damage.

Athos ducks the swipe from the dragon but loses his footing  on the loose sand as he attempts a counter strike.  Rolled a natural one on the attack.

umfir casts Guiding bolt at the dragon.

Attack: 21, Damage: 18