The Sacred flame just passes over his shoulder and misses.

Status
Blue Orc: (-2)
War Chief (-62)

Sly, Eggo Lass and Salamander are still up!

[Also this is Post #1000! We're near the end of Dungeon 5, so if we continue for the rest of the campaign at a similar rate, we might end up with over 20,000 posts, which is both terrifying and exciting! Obviously that's just a rough estimate though, as some dungeons are longer or shorter than others]

Disappointed that the fireball did not work he decides to go and cheer up the team.

"Rah rah!" The goblin shouts, raises up his fists with both daggers, swinging them side to side in the air. "Sis-boom- STAB!" And then he stabs the War Chief. He just cackles a weird laugh.

((Action: Attack @War Chief with Dagger 15 + 4 = 19 with 5 damage))

He goes in again but this time misses. Salamander swings his aim too hard and trips over his own feet. 

((Action: Attack @War Chief with Dagger 5 + 4 = 9 with what would have been 6 damage)).

"Ahhh! Ahh!" He makes some sort of noise as he goes and tries to scramble away on all fours. Somehow he stays in one place for a bit before actually scrambling out of the way, though not enough that he would like.

((Bonus Action: Hide with Stealth of 11 + 2 = 13))

With the wand emanating darkness still clenched in her teether, Eggo Lass draws her second dagger and lashes out at the war chief.

Item Interaction: Draw Dagger

Action: Attack w/ Dagger @ War Chief
To-Hit: max(9,7) + 5 = 14
Damage: 2+3 = 5 piercing

Bonus Action: Two Weapon Fighting w/ Dagger @ War Chief
To-Hit: max(17,8) + 5 = 22
Damage: 3 piercing

Sly hears Salamander shouting up ahead from somewhere within the darkness, making it easier to pinpoint where she shouldn't shoot.

Repeating her gathering of heat, she sends another fiery missile towards the orc chief.

Attack: 12, damage: 10

Salamander and Eggo's daggers strike the War Chief, and just manages to recoil back to dodge the flaming beam sent by Sly in the darkness. He then twists and slams down his greataxe at Eggo Lass, despite being unable to see, then throws his spear at Sly.

War Chief (-70): Multiattack: Attacks Eggo Lass with his Greataxe at disadvantage: 12 to hit, 16 + 5 slashing damage.
                                                   Attacks Sly with his Spear: 12 to hit, 9 + 4 piercing damage.

Everyone is back up for initiative again!

Slys hands are starting to get uncomfortably warm, as she continuously heats up more and more matter to sling in the direction of the orc. Alas, she didn't have many other options at the moment. Straying too far into the darkness would mean a quick end at the orcs blade, that much was certain.

A spears barely misses her, clinking into the stones behind her. Cold sweat runs down her back. This was getting desperate. She had to be really careful with this next attack, or it would be her last.

Fire bolt attack: 24, damage: 8 fire

Eggo Lass dodges out of the way of greataxe, comfortable in the darkness. (You merely adopted the darkness.) she telepaths to the war chief, (I was born in it. Molded by it!)

She dances with her daggers, striking at the war chief.

Action: Dagger @ War Chief
To-Hit: max(5,10) + 5 = 15
Damage: 2+3 = 5 piercing

Bonus Action: Dagger @ War Chief
To-Hit: max(6,5) + 5 = 11
Damage: 4 piercing

(Nice hits.) she adds to her companions.

The fire bolt strikes and singes the forearm of the War Chief, but he still manages to step back away from Eggo Lass's dancing blades, as if he anticipated them. He utters in the gloom, a singular phrase, the first true sentence you've heard from him 'We will all be molded by the darkness eventually. Don't you see we've all been encased in Shadows since you entered these dungeons?'

Status
Blue Orc: -2
War Chief: -78

Just Salamander and Graelor left now!

(Can Graelor see the Orc War Chief or is he still encased in darkness?)

[Graelor backed away to get out of the darkness and the War Chief is still in it but no disadvantage or advantage on either since you can’t see him and he can’t see you] 

(If I was to cast Guiding Bolt on the War Chief from where I am at, what would my chances be (ADV vs. DIS, penalties, etc) with my Sentinel Shield Perception bonuses. I'm trying to decide what to do)

 Which party members do I see?

You’d get no advantage, disadvantage or penalties with Guiding Bolt against the War Chief, and would get no bonuses from the Sentinel Shield especially since Guiding Bolt doesn’t require sight. 

You can see everyone aside from Salamander and Eggo Lass if I’ve read through the posts right. 

Graelor summons all of his strength and focuses on the area where he believes the War Chief to be and summons his Guiding Bolt. With a quick glance to the heavens and a final plea to Helm for his blessings, he hurls his GUIDING BOLT into the darkness at his enemy.

Roll to hit, (4)+5=9 Probable miss. Damage would have been a 15 if it would have succeeded. 

Graelor looks up to the heavens and wonders why he is being tested this way

The blinding bolt fades into darkness, yet you hear no cry of pain. 

Just Salamander now!

Salamander really really wants to bite something now. His sharp fangs are just dripping with envy (well, acid actually) for his daggers. They want to pierce through skin so bad. To rip and tear. Oh ho ho ho so good. The goblin smiles, puts any his actual weapons, and decides to (yes!) use his teeth. He runs in where his Primal Savagery acid-laden teeth take to the War Chief's leg like a dog with rabies.

((Action: Attack @War Chief with Primal Savagery 15 + 4 = 19 yess; Acid Damage: 3))

 His teeth sink in. You can tell he is having fun with it. Muffled, he makes laugh-growling noises at any attempt to kick him off. "RAHAHAH HAHAH RAHHHH!" He nearly refuses to let go. It is not until he realizes that the orc will most likely swing at him again that he hops off and darts out into the darkness. He hisses.

((Bonus Action: Hide with Stealth 18 + 2 = 20))

Salamander's acid-lined fangs sink into the flesh of the War Chief and despite the little damage actually dealt, he seems more than irritated by this. He's even more annoyed when he feels the teeth withdraw and sense the attacker move back into the darkness out of his mental map of the room. Deciding he's had more than enough of the dark, he slashes out twice at Eggo Lass to try and subdue her, then tries to pass her through the darkness and out into the brighter gloom of the throne room, ready to attack some more meddlesome enemies.

War Chief (-81): Multiattack: Attacks Eggo Lass with his greataxe at disadvantage: 12 to hit, 8 + 6 slashing damage on a hit.
                                                   Attacks Eggo Lass with his greataxe at disadvantage: 16 to hit, 7 + 3 slashing damage on a hit.              

Everyone is back up in initiative! Eggo Lass can make an Opportunity Attack against the War Chief, who is now out of the darkness!  

The second hit, causing Eggo Lass to have hold her concentration.

CON Save: 9+3 = 12
DC 10, Darkness stays up

As she grunts from the savage attack, she strikes out with her dagger in retaliation. (opportunity attack)

To-Hit: max(9,1) + 5 = 14
Damage: 2+3 = 5 piercing

(What's the matter?) She telepaths. (Don't want to play no more?)

She chucks her daggers at the orc and then readies her wand once more in her hands.

Action: Dagger thrown @ War Chief
To-Hit: max(2,10) + 5 = 15
Damage: 1+3 = 4 piercing

Bonus Action: Dagger thrown @ War Chief
To-Hit: max(10,4) + 5 = 15
Damage: 3 piercing

[[ IIRC a 15 didn't hit last time. So three attacks all with advantage and not a single hit. Not a single die out of 6d20 above a 10. I'm a little bummed out, man. :P ]]

Item Interaction: Take wand out her teeth and back to her hands.

She smiles at Salamanders skilled hiding. "I like your spirit, little one."

[That's a shame, really poor odds on that one!]

The first dagger takes a swipe at the War Chief yet he just powers past, and he barely even turns around to see the two daggers flying out of the guise of darkness only to pass straight over his shoulders. He cackles and says 'Gruumsh is giving me luck! You say you were moulded by the darkness, elven one, yet it will turn on you, just you wait!'

Salamander, Graelor and Sly left! The War Chief is out of the darkness and still on -81!

Graelor pictures the War Chief in his mind and casts SACRED FLAME. The War Chief needs to make a DEXTERITY saving throw DC13 or take 6 points of radiant damage.

The War Chief mutters under his breath 'Gruumsh, in you divine powers, allow me holy defence against this sacred flame', before taking a literal leap of faith to the side to try and avoid the incoming beam of radiant light. Dexterity Saving throw: 2