Gangplank vs Tryndamere

Build a chain with Powder Keg (E): detonate the keg farthest from your opponent, and each keg whose area touches the previous one explodes too, all the way to them.

Last-hit minions and pop kegs with Parrrley (Q): a kill with the shot gives bonus gold, and so does a kill from a keg it sets off.

Save Remove Scurvy (W) for a key CC rather than for healing: it cleanses all CC on you, on a 22 to 14 second cooldown.

Cast Cannon Barrage (R) anywhere on the map to help a fight or cover an objective: each wave of cannonballs slows and damages in the area.

Avoid taking a trade when his Fury is high: with Battle Fury (passive), it raises his critical strike chance, and Bloodlust (Q) turns it into healing.

Hit him when he walks up to minions to farm: each last hit gives him Fury, which Bloodlust (Q) then turns into healing.

Against Mocking Shout (W), back off sideways rather than turning your back on him: the spell only slows enemies who are facing away from him.

Once he hits level 6, plan for what comes after Undying Rage (R): he can't die during the effect, so back off or hold any CC you have, and finish him when it ends.