Way back in the day (waaay back) I used to play DOS MAME with two sidewinders all of the time. The trickiest part was finding a sound card with a game port that would support two sidewinders at once.
I had a Packard Bell P150 with some cheaply built sound/modem combo card and it played two sidewinders like a dream (ahh those glorious days of Callus--Sardu, why did you forsake us?). Then when I upgraded to a home built computer I never could find another sound card that would allow me two play with two Sidewinders at once in DOS (Windows no problem). I tried Ensoniq PCI (one Sidewinder only), Soundblaster 16 ISA (one Sidewinder only), Soundblaster AWE32 PCI (no gamepads at all in DOS)...you get my drift.