The best bet for scalper tickets is on Front St, right opposite Boston Pizza. You will see (and hear!) a heap of scalpers around there, and you can use them to get a better price also, keep walking up the stairs and there will be a lot more scalpers. Make sure if you have an accent you say you live in Toronto - or else they will overcharge ya.

There is a reputation among Toronto scalpers that they are the most successful in the world, which is largely due to the Maple Leafs. This is most evident by the fact that when you go to an Olympic Games anywhere in the world, it is very likely that if you talk to a scalper at an Olympic Games event, they are from Toronto. The other thing to take note is that they work in teams, so if you try to bargain with different guys, it is likely that they are working all for the same 'guy/team'. If you come from out of town, they can take advantage of you. However I am from out of town myself and got a signifiant discount once because a scalper thought I was English AND a Manchester United fan (blasphemy) so he gave me $50 off. The best advice is to look online on StubHub to get an idea of what the market is like. If you go to a Yankees-Jays fan, then don't expect too much of a discount. However if Milwaukee, Colorado or Arizona are in town, then you may have a bit more of an opportunity to get yourself a good deal.