OOC: I'll say roll Acrobatics(I believe there is a specific roll but I cant think of it right now.)I will say that you will risk getting Ivellios tied up with it since he's basically right on top of him, holding him there.

Acrobatics 19

26

You are able to entangle the creature but you also trap Ivellios with it.

To all those next to the pipe, you here the sound of clanging as several rocks descend from the pipe.As the rocks spew out from the pipe, I need anyone standing next to the hole to make a Dex save DC:13. Ivellios and Doomsday make it with disadvantage, since they are wrapped up together.

Doomsday Save:14 

The rocks fall landing on the trap door which doesn't open immediately and instead seems to take a few seconds, before it opens and allows the rocks to enter the grinding machine.

DEX save: 18

Or 7

[Forgot about the disadvantage]

Ivellios takes 11 bludgeoning damage from some stray debris the spews from the hole, while Doomsday only takes half. From what you guys have seen this trap door seems to be on a timer and will open again after Quintoc's next turn.

Its Lari's turn.

Lari is prone on the ground and tries to roll away from the falling rocks. DEX save: 23. He uses half of his movement to stand up then dashes to help Ivellios get free of the rope. Scamp does his war dance and tries to distract the golem.

As he helps Ivellios Lari shouts, "This is a servant of the Lady! Someone see if the lantern will work to calm it for a moment!"

It's Byg'wygg's turn then. 

Byg’wigg destroy Doomsday! Byg’wigg shall win! “Hey yous! You is nothing! You is nobody! You no amount to nothing in this world!” Byg’wigg use Beg, Grovel, and Cower to give all allies advantage on attacks against Doomsday.

Sorry, Ivellios! Aaagh, rocks!

Dex save 10

Quote from JcAndD >>

Byg’wigg destroy Doomsday! Byg’wigg shall win! “Hey yous! You is nothing! You is nobody! You no amount to nothing in this world!” Byg’wigg use Beg, Grovel, and Cower to give all allies advantage on attacks against Doomsday.

Athletics: 8

The creature breaks free of the grapple. It raises it arms high into the air, forming the familiar clubbed fists it has been using. For a second, ivellios, you think its going to bare down on you, holding nothing back. But, surprisingly, its attention seems to be drawn from you. Following its line of sight you see that it is staring at the remaining pile of dream sand off to the side, beneath the broken tube. It lets a low grumbling sound, lowering its arms and begins moving toward the pile.

Making a Dex save(because rope):19

The creature ignores the rope and walks 15 feet toward the pile, pulling Ivellios with him. Everyone who wants to can make an AOO on him.

Whack him with dreamsand stick! Attack: 14 Damage: 3 magic bludgeoning damage.

(Lari's bow is out. Can he draw his rapier to stab at it?)

Attack: 21. Damage: 7.

OOC: Yes but you will be dropping the bow to the ground to attack with the rapier.

Quintoc will stab at him.Attack: 20 Damage: 14

Quote from ShyVideoGamer >>

The creature breaks free of the grapple. It raises it arms high into the air, forming the familiar clubbed fists it has been using. For a second, ivellios, you think its going to bare down on you, holding nothing back. But, surprisingly, its attention seems to be drawn from you. Following its line of sight you see that it is staring at the remaining pile of dream sand off to the side, beneath the broken tube. It lets a low grumbling sound, lowering its arms and begins moving toward the pile.

Making a Dex save(because rope):19

The creature ignores the rope and walks 15 feet toward the pile, pulling Ivellios with him. Everyone who wants to can make an AOO on him.

OOC: It will be your action to try and break free Ivellios.

Ivellios is unable to break free of the ropes and is dragged with the creature 15 feet. 

Quintoc's turn.(You hear the rattling of rocks in the pipe above you.It would probably be best to move before they get here.)

OOC: I gave Advantage to everyone’s attacks, just remember that.

Quote from JcAndD >>

OOC: I gave Advantage to everyone’s attacks, just remember that.