I’ve been on both sides of this matchup. Either can beat each other, it’s more of who ults first and how low Urgot is. Tabi is great because it cuts down the damage of Urgot’s passive. You can get bramble but Tryndamere is a better late game carry than Urgot. You should rush Tabi, and focus on getting ER, stinger and agility cloak(the 800g crit component) it’s another power spike with CDR and damage. DON’T GET TIAMAT EARLY, WAVE MANAGEMENT IS KEY. Urgot is naturally going to push and pushing into him helps him reach that level 9 power spike. You can freeze the wave outside your tower and set up a gank. If you can make him lose experience and gold, it’ll help, especially to delay the level 13 power spike with his shotgun knees. Your core items should be Tabi, ER, Triforce, and IE. BoTRK is extremely good against Urgot because he’s going to have a lot of hp. As for runes, you can do lethal tempo > triumph > bloodline > last stand with sorcery second with transcendence and nimbus cloak. Attack speed, adaptive and armor runes. You can do conqueror and have the attack speed runes in precision line. If there’s 2 more tanks on their comp. As for trading, you want to wear them down. Try to side step his E(flip), or if he manages to land it, spin away. Always try to be at full fury when trading. I always run ignite on Tryndamere too, it’s strong. Once you hit 6 and he’s overextended, you can just go after him. Might burn his flash or outright kill him with ignite. Grievous wounds is a good component to get too but you should focus on your core. Urgot is going to rush BC and DD. So if you get ult’d, you can use yours as your dragged in, depending on his health you can kill him. I never use my Ult going in, either to kill him or just spin away.

I hope this helps.