Roger Federer has just won another award (in 2013 - one of his worst seasons) in his career and Tim Henman commenting on the ceremony says ironically:
He will probably win (once or twice more/again) the fans favourite even when he is not playing.
I wonder why my teacher says "When he does not play" would be wrong and that it would imply just one match. However my intention is to say "When he does not play" = when he is retired.
Is it really wrong? What is the difference please?
Thank you!