Camp Woo Hoo didn't actually lose the games. As Woo Hoo ran past the last member of Hoo Rah, a boy in a blue shirt has his arm out and touches her. Since there are no more members of Hoo Rah, Camp Woo Hoo can bring the flag back at their leisure since no time limit was ever mentioned.
There's no mention of why Woody no longer lives in his custom built house by the river that Tommy's dad built for him.