Tundra:

Errich strikes quickly and unpredictably and drunkenly, as he stumbles away, but he doesn't penetrate Crows defences (Flurry of Blows grants him disengage without the use of an action as part of his archetype. i-9?)

(Hammerstone. Talmich is unconscious)

(Perception to contest stealth: 19

Pits: 

Calgin spots four Pollys at G-2. The birds hold their Silver Rapier.

(Calgin)

Arena 3: The Pits

   A  B  C  D  E  F  G  H  I  J  K  L  M  N  O  P
10  .  .  .  .  .  .  .  .  .  .  .  .  .  .  .
 =..%=========================================%..
09  .  .  .  .  .  .  .  .  .  .  .  .  .  .  .
 =€==.....======///......=......///======.....===
08  .  . Q.  /  .  /  .  =  .  /  .  /  .  .  .
 =.....======/....../////=/////....../======.....
07  .  /  .  .  ,  .  .  .  .  .  .  .  .  /  .
 =...../..................,,,.,,.......,,,./-----
06  .  _  _  .  ,  .  .  ,  .  .  .  .  _  _  .
 =.....______.........,........,,.....______.....
05  .  _  _  .  .  .  .  .  ,  .  ,  .  _  _  .
 =-----/....,,,.........,,................./.....
04  .  /  .  .  ,  .  .  .  .  .  .  ,  .  /  .
 =.....======/.,,.../////=/////....../======.....
03  .  .  .  /  .  / 8.  =  .  /  .  /  .  .  .
 ====.....======///......=......///======.....==€
02  .  .  .  .  . C.  .  .  .  .  .  .  .  .  .
 =..%=========================================%..
01  .  .  .  .  .  .  .  .  .  .  .  .  .  .  .  
   A  B  C  D  E  F  G  H  I  J  K  L  M  N  O  P

Key: '=' High wall (8ft.), '-' Low wall (2ft.), '/' Drop into pit (10ft.), '_' Steps (4ft.), '€' Tree, '%' Door, '.' Dirt, ',' Grass, 'A-Z' Contestants

Finally catching sight of his foe, Calgin moves in and swings twice at the birdman with his greatsword.

(Assuming he's still at G2 or close enough for me to reach with my 40 foot walking speed.  If he's moved further away, then dash and use charger feet to melee as a bonus action.  In that case, add +5 damage to the first attaack and ignore the second)

Attack: 14 Damage: 20

Attack: 19 Damage: 18

(Whoops, should be +1 more damage on each of those from hybrid form)

Mirror Image target roll: 6

Pits: (Round 4)

Calgin rushes over and strikes at Polly. The bird pops like a balloon. He strikes again (which? 15)... A second Polly pops.

(Polly)

Polly strikes back with the silvered raiper Attack: 14 Damage: 10

(What form is he in only rolling regular dmg, not sure how you want dmg done if it hits and he is in werebear form)

Disengage to K2

(I'm in wearbear form, but using my greatsword still.  Vulnerable to silver so I just take double whatever damage you roll)

Pits: (Round 5)

Polly stabs at his foe, wounding the monster badly.

The Panther climbs effortlessly to the ledge and strikes at Calgin, biting 22 for 6 piercing. (Which? 11) Calgin is hit.

[Edit: Polly moved, the panther targets Calgin.]

(Just roll damage ignoring resistance or vulnerability then double or half accordingly)

(Calgin. Wis save)

(Just wanted to make sure that you saw that I disengaged and moved to k2, just trying to keep strat where every enemy is on in the arena) Nevermind saw your edit.

Wisdom: 21

Calgin tosses another fuzzy ball from his bag to land next to Polly, summoning a...1 Giant Goat.  "Attack Polly!" he orders, then retreats behind the walls.

Move around the west edge of the pit, trying to move as quietly as possible. 20.  Not very quiet.

(Just realized my weasel earlier should have actually been a rat, was looking at the wrong bag.  not that it changes anything that happened)

The goat attempts to ram Polly.

Mirror Image? 5 Attack: 9 Damage: 8

Cast Shadow Blade and Attack Billy Attack: 22 Damage: 28

if goat dies Move to C8,

The Goats head flies through the air in view of the Beartle.....

Hammerstone will take a strike at Crow. 

Attack: 25 Damage: 8

Bonus action, second wind: 11

 (I'm assuming I need line of sight to be able to use my blood curse of the eyeless?)

(nvm)

(Just gonna do my turn now as ill il busy for most the day.) Morthos will fire an arrow at Errich.

Attack: 23

Damage: 6

As a bonus action i will cast Hail of Thorns doing 10 Damage.

Dex save 11- on success half that.

Pits: (Round 5)

Calgin keeps his wits and summons another ally. It rams a Polly the puffs away like mist. He attempts to keep quiet (Effect: 3, the loser suffers disadvantage on their next attack against the winner this round, Contest with Perception or Investigation.)

Polly produces a sword from the mist and decapitates the short-lived foe and flies away.

(You don't need to see to use your Blood Curse, but I won't let you target an enemy with total cover.)

The Panther attacks again, biting 16 for 6 piercing. Typical cat vs. turtle situation.

(Calgin)

Arena 3: The Pits

   A  B  C  D  E  F  G  H  I  J  K  L  M  N  O  P
10  .  .  .  .  .  .  .  .  .  .  .  .  .  .  .
 =..%=========================================%..
09  .  .  .  .  .  .  .  .  .  .  .  .  .  .  .
 =€==.....======///......=......///======.....===
08  .  .  .  /  .  /  .  =  .  /  .  /  .  .  .
 =.....======/....../////=/////....../======.....
07  .  /  .  .  ,  .  .  .  .  .  .  .  .  /  .
 =...../..................,,,.,,.......,,,./-----
06  .  _  _  .  ,  .  .  ,  .  .  .  .  _  _  .
 =.....______.........,........,,.....______.....
05  .  _  _  .  .  .  .  .  , C.  ,  .  _  _  .
 =-----/....,,,.........,,................./.....
04  .  /  .  .  ,  .  .  .  .  .  .  ,  .  /  .
 =.....======/.,,.../////=/////....../======.....
03  .  .  .  /  .  /  .  =  .  /  .  /  .  .  .
 ====.....======///......=......///======.....==€
02  .  .  .  .  .  .  .  .  . 5. Q.  .  .  .  .
 =..%=========================================%..
01  .  .  .  .  .  .  .  .  .  .  .  .  .  .  .  
   A  B  C  D  E  F  G  H  I  J  K  L  M  N  O  P

Key: '=' High wall (8ft.), '-' Low wall (2ft.), '/' Drop into pit (10ft.), '_' Steps (4ft.), '€' Tree, '%' Door, '.' Dirt, ',' Grass, 'A-Z' Contestants

(The blood curse would have been to keep the goat alive.  Also, you seem to have skipped my movement in my post)

(Do you use it?)

(Assuming yes, on follow up.)