Okay. So if you were able to predict your friend's winnings and used the 11th house, then the 11th house does work as an indicator of winning in horary charts.
Applying this to Darkgirl's question, she will win as her ruler makes a sextile to the ruler of 11 (Moon), but it won't be a huge amount as Mercury is retrograde. I think Moon's sextile to Neptune adds luck to this scenario as well.
Regarding Jupiter in your chart, do you have a day chart or a night chart? (Chris Brennan's video)
Applying this to Darkgirl's question, she will win as her ruler makes a sextile to the ruler of 11 (Moon), but it won't be a huge amount as Mercury is retrograde. I think Moon's sextile to Neptune adds luck to this scenario as well.
Regarding Jupiter in your chart, do you have a day chart or a night chart? (Chris Brennan's video)