Tryndamere vs Gangplank

Keep your Fury high before a trade: with Battle Fury (passive), it raises your critical strike chance. Spend it with Bloodlust (Q) when you need health.

Cast Mocking Shout (W) before a trade against a physical damage champion: it lowers their attack damage, and slows enemies who turn their back on you.

Count on Spinning Slash (E) to stick to your target or to escape: each critical strike lowers its cooldown, more so on a champion.

Wait until you're close to death to cast Undying Rage (R): you can't die during the effect, and delaying it pushes the enemy to take risks to kill you.

Split push in a distant lane to draw several enemies: Undying Rage (R) helps you hold them off while your team takes an objective.

Destroy his kegs before he does: a Powder Keg (E) destroyed by an enemy is defused, and each keg loses health over time.

If you can engage, go all-in: his kit has no dash to escape.

If your team has several CCs, don't use them all at once: Remove Scurvy (W) cleanses all his CC, then has a 22 to 14 second cooldown.

In teamfights, get out of his kegs' area: each Powder Keg (E) explosion deals the damage of the attack that set it off, ignores part of your armor and slows you.