gerund and infinitive

[user_gary]

When we should use `infinitive' and when we should use `gerund'

e.g. I fail to win match
I fail winning match.

What is the difference in meaning?

Also, what is the difference in the usage of `gerund' and `infinitive'?

[Tdol]

I fail to win match
I fail winning match

I am afraid that often it is just a question of learning whether a verb if followed by a gerund or an infinitive. There are verbs where you can use both and there is a difference in meaning:
I stopped working.
I stopped to have lunch.
In the first, I did not work any more (one action). In the second, I stopped one thing so that I could do another (two actions).