No. After all, there's a $50 limit on the regular bets and you can't just put the same bet on twice to make it $100. Well, the same goes for the free $100 bets. You can't put exactly the same bet on 5 times. Having said that, there's nothing at all to stop you having $100 bet on a team to win, another $100 on them to win by a certain margin, another on them with points start, another on the half time/full time double etc etc. So you can certainly have 5 different bets on the same team, just not the same bet 5 times.