I was in this game against Cow and Aloullette and few things didn't go their way for the following reasons:
1) Cur2 vs Cur1 (as the game progressed to giants, they clearly didn't have the money to support the upgrades)
2) 2 kills vs 7 kills when the giants rolled in (again didn't have enough money to do any upgrades)
3) When an oak has 0 kill in the late game, you can't justify purchasing a Jboot. Note that, Jboot is one of my fav item and it not only gives you the speed but also HP (great for HP stackinig)
4) Cow's team did have a good control of the flag and did capture our portal at one point, but they didn't have the creeps to support it. We were just hitting Cow (UB) first and his mates didn't do much to support him.
I think the game would have been different if the money was spent on the citadel instead of the jboot. When I play ere/oak, i usually go with narmoth, 2helms, unbrk boots, wand of speed, then sell everything except the 2helms to support the cita near the end.