"Mn... After next match." Gimmond mutters after giving his funds a once over. When he reunites with the others and share their collective findings, he nodded understandingly at Athos. "Same goes for me, but.... I've heard of another unit tangling with it before. Darkness will not be any ally of ours when facing it. If anything, it'll be the exact opposite, as they retain a few of their old Drow abilities. And if its one, odds are the arena will be shaped to only make it that much more of a challenge." 

Zumfir appears to pale with the knowledge of the next enemy. "A. . . Drider." He echoes, his voice a bit shaky. The elf looks down, taking a deep breath, before whispering a prayer to himself. "I see . . . they are . . . strong creatures. As Gimmond says, they are stronger in the dark. Luckly, i know a spell that creates sunlight." He comments, opening his hand to show a small ball of radiant light. "There won't be darkness for it to hide from us. Just kill it, before it kills us. The usual."

"Kill it before it kills us.  Sounds like a good plan to me."  Athos will clean a bit of his armor as he waits for the next round to begin.

(oops, forgot to post here and then it dropped off my notifications. Will start once I wake up) 

You enter the arena and it has returned to its normal appearance. This time however, despite being daytime, the light has all been blocked out and you are fighting in dim light as the sky within the arena is locked in twilight.

As expected, a drider appears, and you all get to go first 

Athos takes a brief moment to cast a guiding bolt at the drider (23 to hit for 10 radiant damage), he'll chase after his spell to get as close as he can.

*On a hit the next attack will have advantage against the drider.

Twinkle cracks her knuckles. "Then let's get this party started!"

The monk rushes forward, guided by Athos' light, going for a kick right where she supposed the Driders upper body connected with the lower one. She focuses her energies into that singular attack, attempting to overwhelm the monstrosities defenses and stun it.

Action:
Attack 1 [adv from Guiding Bolt]: 20/14, damage: 13 force + [Stunning Strike] [Con Save 14 or be stunned until start of Tinkles next turn]
[All further attacks are rolled with advantage if the stun is successful. If it is, take the higher number, otherwise take the first.]
Attack 2: 26/18, damage: 12 force
Bonus Action [Flurry of Blows]:  
Attack 3: 12/13, damage: 7 force
Attack 4: 26/28, damage: 13 force

Gimmond was a bit leery of leaving Zumfir behind, but she'd more than proved herself a tough one. So, he rushed in as well, hot on the hills of his fellows! Then the moment comes for him. During that brief window in which the drider appeared distracted by the others he unleashes an unrelenting barrage of attacks at every weak point, as no attack of his fail to find their mark without leaving behind more than just a mark!

Mo: Into melee with Drider.
Ac:
Attack #1: One-Handed Vicious Spear vs  Drider(AC ??) - To Hit: Nat 20(for 27 total) For: 21 Piercing Damage.  (Rolled a 2nd time w/ Savage attacker and more or less wound up with same results)
But if hit, target is Sapped.
Attack #2: One-Handed Vicious Spear vs  Drider(AC ??) - To Hit: Nat 20... Again! For: 19 Piercing Damage. (Accidentally rolled part of the damage twice despite SA only being one turn, so ignore the 14) 
Ba: Polearm Strike vs Vicious Spear(AC ??) - To Hit: Nat, freaking, 20!! For: 25  bludgeoning damage. 

(OOC: I really wanted to add maneuver dice on each of those, but since all I got that might be applicable is Maneuvering Attack, but didn't feel it appropriate)

Zumfir points his mace towards the arena, summoning a giant ball of light, completely basking away the darkness. "You won't fight in your domain, Beast! I claim this arena as Eilistraee's domain now!"

Cast: Daylight

Athos gets an initial hit in, setting up Twinkle for her first hit. 

It saves against the stunning strike (save 20). But that doesn't change any of the other results. The third attack from Twinkle misses and every other attack hits.

And then Gimmond absolutely decimates the creature. It is very critical (10hp remaining....).

The daylight causes the drider to recoil, giving her disadvantage on all attacks and checks. To try and gain some advantage back, she draws on some innate magic and casts web as a bonus action, to target all of you. I've rolled for Gimmond as it affected her attacks, and he failed so is restrained (so her attacks on him and now a straight roll as daylight is canceled by restrained)

She attacks three times but only two hit (24, Nat 20, and 11) for a total of 32 damage. You are all up and this is another short round (which means next round will hopefully be more deadly) 

Athos got a 5 for his save, so he was restrained as well.  He will try to break free with a 17 for his athletics check.

Ah yes, the dc might help. Dc14 so Athos is free now (but used his action) 

Twinkle hops away from the net, avoiding the sticky substance. [Dexterity Save: 22]

If it seems feasible that Twinkle can rush around the net and attack the drider in melee, she will do that. If the drider is standing in the middle of the web, Twinkle will instead start throwing daggers.

[The first two attacks will be the same, except for the attack bonus. If Twinkle needs to throw daggers, subtract -2 from the following attacks]

Action: Attack
Attack 1: 14
Attack 2: 17

[Alas 😔]

If Twinkle was close enough to attack in melee:

Bonus Action: Flurry of Blows:
Attack 3: 28, damage: 11 force +  [Stunning Strike] [Con Save 14 or be stunned until start of Tinkles next turn. What I forgot before: If the Drider succeeds, it's movement is halved for the same duration and the first attack has advantage. Immediately applied to attack 4.]
Attack 4: 22/13, damage: 7 force

If she was not close enough to be in melee:

Bonus Action: Elemental Attunement, empowering her strikes with reach and elemental damage for next turn.

Gimmond was practically coughing up blood from the Drider's retaliation, but refused to yield! Digging deep, he not only managed to center himself enough to break out of the webbing, but after sucking in a steadying breath, lunged at the creature ready to finish the job with a flurry of his own spear strikes had Twinkle not beaten him to the punch!

Ba: Second Wind, regaining 15 Hp. 
Ac: Attempt to break out with a 8, which is a fail. Spending another use of Second Wind for Tactical Mind to add 9 to the check, turning it into a sucess with a 17!

Action Surge!

Ac: Attack vs Drider.  
Attack #1: One-Handed Vicious Spear vs  Drider(AC ??) - To Hit: 22 For: 17 Piercing Damage.  
But if hit, target is Sapped.
Attack #2: One-Handed Vicious Spear vs  Drider(AC ??) - To Hit: 21 For: 19 Piercing damage. 
(Attacked twice for if target is somehow, SOMEHOW still standing)

Twinkle was already in melee and nobody had moved so she can still reach. I'm not rolling the save for stunning strike as the damage was enough.

The whole arena is bathed in light as the artificial darkness fades (no difference to you guys as you already had sunlight), and as you leave, you gain 250gp and one uncommon magic item of your choice. 

Athos will give his customary cheer to the crowd at their victory before heading out.  He will pick up an uncommon Amulet of the Devout as his reward.

Athos' Insight: dirty 20

"That was . . . weird." He commented. "What was a drider doing here . . .and why . . . did it agreed to fight? Probably, the servants of the spider queen thrive on chaos." Zumfir comments to himself as they left the arena to heal.

Insight: 18

Twinkle shakes out her fist. "That spider carapace was pretty hard. Though it seems unfair to send a single combatant against all four of us!"

The monk picks up an Immovable Rod. Who knew when that would come in handy!

She has a listen for rumours as well: Perception 15

With that match out of the way Gimmond not only followed through on an unspoken promise and bought the one ring, but picked a Lantern of Revealing Light as his reward from the last match! "Either that or the blighter was captured following some surface raid, and slated for execution anyways. Regardless of the reason, it was good we put it down. From what tales I've heard it lives a tortured existence as a punishment, not reward." Mentions the dwarf before he goes off to get some oil, a drink, and for the local news.

Meant to put that in quotes, not spoiler AND forgot I was at a +4 not 3, so that's a 20 Perception and 1,001 gp spent between the ring of swimming and 10 flasks of oil.