OK, I managed to get it going - finally!
First off, the machine is running ClassicWB on a CF2IDE adapter. With this comes iGame by default. I added the Speedball2_V1 archive from whdownload.com, then after adding the game into iGame, selected the game and selected "Game Properties". Then above the tooltypes style list that says "*** DONT EDIT etc", added a line that says "NOCACHE".
Voila ;-)
Now, if anybody know how I can save my games that would be great. When playing Leage it sometimes shows "SAV" but not always...