The entitled manager is not associated at the winning time. Check the cup final:
http://www.rubysoccer.com/game/match_report/88974
Manager: Rodrigo Mascarenhas
The winner is the manager of the last game of the competition (like the cup final, the last league match), not the manager at the end of the season.
Cheers

We are aware of that problem Hugo, currently we only create these kinds of events at the end of the season, that’s why you’re seeing the wrong information. It shouldn’t be hard to create the event when the competition ends, specially for national cup and international cups. Thanks for reporting, even though we have that on our list it’s good to be reminded of some bugs so we can raise their priorities ;-)

Cheers!

Should be fixed, next time a competition ends (except for leagues) the history entry will be created.

Cheers!