Why did Roy lose the match?

Reality. When competing professionally, everyone loses since there is only one person that gets the 1st place. Thus the protagonist couldn't win, it was already ridiculously exaggerated that he came so close whilst being handicapped.

But life moves on and you can't allow yourself get stuck in bad moments as Harelson did in the start of the film. In the end he learned his lesson and seeked happiness elsewhere.

Maybe they didn't want to go for the cliche about him winning the big game. In a way, I liked that because I was surprised they did that. Of course, Roy still wins in a way. He gets Claudia and has a job now and is making money so his life is in order again and is no longer drinking.

It was worth it just to see BM shake his rubber hand and throw it into the crowd.

Roy sums it up at the end . . .

"You know that old centurion's faith thing... about you saving the Amish people? Well... that was baloney. lt wasn't them you were saving. lt was me."

Roy was a champion bowler but his hubris lost him his hand and his self worth. He gave up trying. In the end, what was important was that Ishmal got him to face his past, stop drinking, and actually try. Roy may have lost the match but he found a new lease on life. If he would have won he may have become Ernie McCrackin'. Rich, arrogant, empty.

Not to mention it was Roy's new found humility that won him Claudia. For all of Roy's money he'll never have a meaningful relationship.

In the end, Roy won more than if he won the championship. He's actually helping people by giving lectures for Trojan condoms and he saved the farm.

Ultimately it was just a great reversal on expectations. 1996 was a great year for unconventional sports movies. I still contend Tin Cup (same year) has the best ending to a sports movie ever. It's not about winning the game but winning on your own terms.

If Roy won, Claudia would have looked like a Golddigger ... Ernie won the money, Roy won the girl!