I’ve been looking for some time now for any games were a far weaker but much more mobile ‘insurgent’ force fights a much stronger but logistically limited opponent.
I’m concerned more with the strategic aspects than tactical ones and the game doesn’t necessarily have to be a war game or even historical.
Hammer of the Scots is the closest I’ve come, can you guys think of any others?
The new Stronghold? Stronghold | Board Game | BoardGameGeek
But that is a entrenched defender facing a ever stronger besieger which isn’t quite what you are looking for.
I assume you checked the standard and weak recommendations on the BGG page. (I’m not very familiar with the games mentioned)
Starcraft (the boardgame)?
I’m thinking ther are games where one can choose the slow/strong vs fast/weak strategy, buyt can’t think of any offhand.
Brian
Would Zombies!!! work ?
I have a veteran wargaming friend who recommends El Salvador.
I believe I came across a game called Idealogy but I never tried it before.
Fox and Geese is an old classic.
A friend and I sometimes play a game called Scotland Yard that might fit your bill. In this game up to four players take the role of the London police, and one person takes the role of a Mr. X, a criminal. The players navigate the city streets and subways of the city trying to capture or elude one another.
The police have superior numbers (there are always four, even if only one player controls them) but Mr. X has the advantage of being invisible for most of the game. The police must try to corral him using clues from the modes of transportation he takes, while Mr. X must use misdirection to throw the police onto the wrong trail.
This game can be game can get pretty intense and requires a lot of thought. It definitely works as a two person game – possibly even better as one because the police will have a more unified strategy without the need to discuss it with others.
A word of warning, though: the roles are very asymmetrical and sometimes people who are new to it perceive this as being unfair. E.g.: “The police have all the advantages, it’s impossible to win as Mr. X”, and so forth. Having played this game a decent amount I think both sides present fairly unique strategic challenges, though Mr. X probably has a higher learning curve.
It’s more RPG than Tabletop, but I can recommend Baba Yaga. Ill get you a link later. It’s a rather… brutal game, without ever feeling unfair. I know. I helped make it.
I’d give it a try, but were the hell do I find it?
I’ve played it and liked it, but that’s not really what I’m looking for.
I’ll look in to the other recommendations. Thanks guys.
Old game…Freedom in the Galaxy. It is about a a group of upstart rebels taking on a big, bad galactic empire (why yes…it did come out after Star Wars…why do you ask?)
The Empire started with large military forces but few ‘leaders’…and was also limited in movement options.
The rebels started out with more leaders and was easier to recruit more.
The problem was that we could never get it to really work. The Empire was too strong even with their restrictions. The manual specifically mentioned that the rebels could not just run from planet to planet starting rebellions because the Empire could just put them down but had to get many planets on the verge of rebellion then push em over all at once. In reality, this was nearly impossible. The attrition rate on leaders was intense for the rebellion and, though they had many more than the Empire, once they were gone, they were gone.
Maybe you’re smarter than we were 
Link to one on ebay
http://cgi.ebay.com/Freedom-in-the-Galaxy-Star-Rebelliions-Bookshelf-Game_W0QQitemZ180434931761QQcmdZViewItemQQptZLH_DefaultDomain_0?hash=item2a02c29031