Your Win Condition
You are favored one through six. The goal is to run down Maokai 10-0 after you buy Black Cleaver.
General Strategy
Play very aggressively one through six. Be conscious of his Grasp of the Undying usage. Maokai Q and R are both bufferable.
Trading Patterns
Maokai will try to use W (Twisted Advance) into Q (Bramble Smash), which is hard to buffer. After he uses W and Q, you can 100-to-zero him. When he has Warden's Mail, be safer with trades. When you press E on Maokai W, you will take him a further distance away.
Wave Management
Their Win Condition
Maokai wins by rushing Warden's Mail, which is the best anti-Urgot item. He also relies on strong gank setup.
