I was able to successfully install Pro Pinball: Big Race USA (from Gamefest Pro Pinball Classics) in a Win98 bottle on the following machine:
Soyo SY-7ISA+ Intel i815 Motherboard
Intel Pentium III 866 MHz Processor
512 MB SDRAM
PNY Verto GeForce FX 5200 AGP 8x 256 MB DDR
Creative Labs Sound Blaster Live! 5.1 PCI Sound Card (SB0220)
Samsung CD-RW/DVD Drive Model: TS-H492A/RSWN
Dual Boot openSUSE Linux 10.3/Windows XP Pro SP3
CodeWeavers CrossOver Games for Linux Version 7.1.2
Splash screens for the developers/publishers display, although the last one is very brief.
There are issues with configuring the game using the in-game menu. Altering the resolution from 640x480 (default) to either 800x600 or 1024x768 causes the game to crash with a CodeWeavers/Wine error and the terminal session has to be aborted. Adjusting many of the other settings, particularly graphics settings, also causes the game to crash.
The game does run with the default settings, but performance is very poor at the beginning of a session when there is an extraordinary amount of hard disk activity which causes frame rate to vary from 1-30+ frames per second. After a few minutes, the problem abates substantially. This poor performance may simply be due to the comparatively old nature of my system.
I have not tested the head-to-head capability of the game.