Hello, I'm Whinja and I've played Urgot for the past year or so. I'm only Gold 5 but I have a good understanding of how Urgot plays and his major strengths and weaknesses as well as ways to mitigate his weaknesses. This guide only covers his matchups against the most popular top laners in the current meta and I will edit it when that meta changes. This is also my first guide ever so go easy on me please :^).

Marks, Seals, and Glyphs are normal for most AD top laners. The quints are a little different from what most Urgot users would take so I'll explain them a little bit.
2 Attack Speed quints help him with last hitting early on in lane. 1 Attack Damage quint is better than 1 Armor Pen quint because Urgot already has a huge natural armor shred

Offensive tree is normal for most AD Casters like Urgot.

The Utility tree is mostly to help Urgot in lane. The extra MS and Mana Regen are huge for his early game, and the bonus potion duration gives him some more sustain as well. The 1% spellvamp/lifesteal is more useful late game, where he can constantly batter people with his Q and heal up off of that. You could put that point into the Runic Affinity if your jungler is going to give you blues otherwise I would stick with the SV/LS.

Starting Items.
Urgot needs boots as soon as possible. There are no other starting items that really help him either, as all Dorans items provide stats that Urgot doesn't really need. Starting 2 health and 2 mana potions allows Urgot to stay in lane longer early on, especially since he goes OOM so quickly.

First Back
Get Tear as soon as possible. Upgrading to CDR boots at this point in the game gives Urgot 20% CDR and extra MS. By this point you should be able to push lane easily into turret (if you haven't taken their turret yet) so the Ward is needed to protect from junglers. At this stage of the game you should just focus on farming up for midgame.

Midgame
This is where Urgot hits a massive power spike. Once you have the Manamune and Last Whisper you will be shredding your opponents. The Enchantment for your boots is unnecessary at this point in the game, but if you can afford it, buy it. The extra MS from Alacrity is crucial pre-lategame. Giants Belt gives Urgot the health he needs to supplement his Armor/MR steroid from his ult.

Normal Final Build
This is what I typically try to end a game with. Frozen Fist gives Urgot some Armor and Mana, but isn't necessary before the other items. The two items that are really needed for Urgot lategame are the SOTLE and the Rylais.
Rylais: Gives urgot a massive slow when combined with his shield's slow. You can kite as long as you have mana or you can perma-slow someone with E-QQQ.
SOTLE: Procs on every single one of your damaging spells. Gives his Q an extra ~16 true damage each time it hits during the E-QQQQ combo. It also procs on every tick of his E, giving him an extra 114 true damage on his E, which already has a large base damage. The CDR also puts him at 30%, which gives him his 4th Q in his E-QQQQ.

If you're really ahead
The Liandries is the only thing I would like to talk about in this part. It gives him a large boost when fighting tanks like Mundo or Nautilus. When combined with Rylais and SOTLE, his E will do 295(+106.8) plus an extra 114 true damage PLUS an extra 20% of the targets health in Magic Damage (4% each second for 5 seconds), theoretically. It also makes itemizing against Urgot near impossible, as he will do Magic, Phyical, and True Damage with each of his spells.

Personal Notes
I have tried and succeeded with this build many times in Ranked as well as normals. It relies heavily on using Urgot's natural ability to kite and perma-slow and enhances these strengths greatly, while giving him a little more survivability and DPS.

Ignore everyone that flames you for picking Urgot.

He typically goes well with poke teams and anti-assassin teams.

Pros
-Does extremely well against melee opponents when he can poke them down with E-QQQ.
-Since he is so underplayed in ranked, people generally don't know his kit that well.
-People underestimate his passive and armor shred.
-Can turn a teamfight by ulting any assassin.
-Ult is great at setting up ganks for your jungler
Cons
-Very susceptible to ganks during laning phase.
-Not the greatest lategame.
-Low MS.
-If enemy laner has a solid gapclose, he loses his advantage in 1v1.
-Requires high mechanical skill to use effectively.
-Not easy to pick up.
-If he loses lane he loses game.
-Sometimes if he wins lane he still loses game.

Try to get a team comp with a lot of poke.
Teams you pick Urgot with
Mid: Xerath/Ziggs/Twisted Fate
Jungle: Pretty much any tank
ADC: Ezreal/Caitlyn/Jinx/Kog'maw/Corki
Support: Sona/Morgana/Janna/Soraka/Blitz

Teams you don't pick Urgot with
Mid: Ryze/Lulu/Fizz/Yasuo/Zilean
Jungle: Any squishy jungler/Maokai
ADC: Graves/Sivir/Lucian
Support: Braum/Zilean/Thresh/Leona