True damage is Volibear's weakness, especially when it is % max health. Vayne has this every 3 hits, and 14% at rank 5 to pair along with it, meaning that you should not look to play Volibear into a Vayne.
Trundle
Trundle presses one button and you become squishy as his ult takes 40% of your armor and MR, also doing % max health magic damage
Zac
Tanky asf, has better sustain due to W, and also ganks more efficiently than you.
Warwick
Healing from almost everything in his kit, has tankiness with E, does magic damage based on % max health with Q, gains movement speed and attack speed with W and also out duels you.
Shaco
Just an annoyance to deal with, and that you cannot build against him until you see what he is building, may it be AD or AP. He has great ganks as well and a flash every 6 seconds so he can run ignite and cut your healing. Turn your back on him as little as possible as he does increased damage to targets facing away from him.
Fiddlesticks
Not played much in my elo but he clears extremely fast, meaning he could pull ganks off faster, something you don't want him to get away with. If he builds Liandry's into Shadowflame, have fun, that is gonna hurt a lot.
Nunu & Willump
Clears faster, ganks faster than you and also has better sustain in the jungle than you.
Rammus
Too tanky for you to deal with, he has a really good gank setup, and you end up killing yourself by fighting him and autoing him.
Kayn
Red Kayn is just a nightmare to deal with; you can't kill him nor outsustain him, he just has so much healing in his kit. Blue Kayn, not a nightmare for you but probably a nightmare for your ADC, he will oneshot almost anyone as get away with it, so you have to peel for your team if ever there is a blue Kayn coming for you.
Jax
Can block your Q with his E and can outduel you. Also becomes tanky with his R and will do more damage due to the R passive (magic damage on 3rd hit).
Mordekaiser
Can disrupt your dives with his R, forcing you to fight him under his turret if ever he ults you when you ult his tower. Also a lane bully so it's best not to dive him. He can also ult you so that you cannot smite objectives.
Master Yi
Your only hope is to invade him to the point he becomes completely useless. If you don't, he just picks people off, gets fed and shreds you with Kraken Slayer + Lethal Tempo. Reason that he is an Even threat is that you can deny his scaling by breaking his tempo by invades or forcing dives.
Teemo
Not the worst but he could block your Q stun with his Q blind. You could dive him at 6 as he is fairly squishy and can be punished for misplays easily.
Gwen
Bad early game but scales. Has true damage in the middle of her Q, basic attacks, middle part of her Q and ult do extra magic damage, equal to a % of max health. Becomes more tanky with W and also has auto reset with E. You might not want to play into Gwen as she will hurt a lot later on. You have to win the early game before she can scale and do a lot of damage.
Irelia
Irelia hurts and can heal a lot with her Q. She is also pretty tanky but you can counter this by diving her early on as your CC can stop her from healing. Can also buy an early Bramble to delay her scaling.
Zed
Somewhat skill-based as you have to time your dives perfectly to where he cannot ult to outplay you or W to escape the dive. If ever you fight him, Q him as soon as possible then throw your E out so that you get the shield and outsustain him.
Katarina
She can escape you easily and has grievous wounds at her ult, making it harder for you to kill her as she could burst you down. If ever she will E towards you, Q her so that she gets deleted as she is still an assassin and slightly squishy.
Yasuo
Barely a problem. Land your Q and E, he will die because of PTA proc. You can also dive him at level 6 as he would still be quite squishy without Immortal Shieldbow.
Lee Sin
If he Q's into you, Q him back. You outduel him early with PTA and semi outscale him late with your tankiness.
Jhin
Everything you want in the enemy ADC. From no escapes to fixed attack speed, he practically has it all: no dashes or escapes in his kit, 4 shots then reload, fixed attack speed in 4 said shots, an ult where he has to stand still for full effectiveness.
Talon
Q him and he is gone. Do not get hit by the return W so that he cannot proc his passive as easily.
Riven
Has a lot of damage but will die if she gets hard CC'ed or has bad mechanics. You need your team to follow up on your Q if ever you will pick her off.
Corki
Dive him at level 6 a few times and he will become useless if ever you get successful dives. Only has W and flash for escapes. Force plays around the map to feed your team even harder so that they can snowball mid and make Corki unable to play.
Kassadin
Dive him at 6 to delay his scaling, force out plays around the map so that you can get your team more fed to end the game before he can scale. Has his ult every 5 seconds at level 6 and a flash for escaping your dives.
Kayle
Same thing as Corki and Kassadin.
Yuumi
You ult at enemy bot tower, she lands her ult, happy dive.
Lulu
BECOME BIG BOI. Also pretty much every shielding enchanter is great with Volibear
Amumu
If ever you get an Amumu support, if he will ult in as soon as you ult into the enemy turret, free double kill for bot lane.
Pyke
Dive into enemy tower with R and Pyke will just execute whoever is low by the dive. Your cut
Akshan
Great dive synergy as Akshan can then dive them with his E without getting hit by turret aggro
Diana
You ult, she goes in and ults, pretty much free if you guys know what you are doing
Miss Fortune
You ult in and she will ult the enemies. If both land perfectly, double kill for Miss Fortune.
Alistar
Disable turret and Alistar will headbutt the enemy out of the turret, then land your stun. Guarantees a free kill if ever it works all according to plan.
Tristana
Ult in, she will W in and do enough damage that she will probably get a double, then she will W out.
Vex
Double the engage, double the trouble. You ult the turret, she ults the enemy laner, enemy laner becomes sad and they die.
Katarina
Your ult lasts shorter than hers does, but I mean, she could burst the enemy in the timeframe of your ult, right?
Qiyana
You ult in, she will burst the enemy laner thanks to disabled turret.
Zed
Same as Qiyana
Yone
Same as Qiyana and Zed.
Synergies
IdealStrongOkLowNone
Yuumi
You ult at enemy bot tower, she lands her ult, happy dive.
Lulu
BECOME BIG BOI. Also pretty much every shielding enchanter is great with Volibear
Amumu
If ever you get an Amumu support, if he will ult in as soon as you ult into the enemy turret, free double kill for bot lane.
Pyke
Dive into enemy tower with R and Pyke will just execute whoever is low by the dive. Your cut
Akshan
Great dive synergy as Akshan can then dive them with his E without getting hit by turret aggro
Diana
You ult, she goes in and ults, pretty much free if you guys know what you are doing
Miss Fortune
You ult in and she will ult the enemies. If both land perfectly, double kill for Miss Fortune.
Alistar
Disable turret and Alistar will headbutt the enemy out of the turret, then land your stun. Guarantees a free kill if ever it works all according to plan.
Tristana
Ult in, she will W in and do enough damage that she will probably get a double, then she will W out.
Vex
Double the engage, double the trouble. You ult the turret, she ults the enemy laner, enemy laner becomes sad and they die.
Katarina
Your ult lasts shorter than hers does, but I mean, she could burst the enemy in the timeframe of your ult, right?
Qiyana
You ult in, she will burst the enemy laner thanks to disabled turret.
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