The test results you have selected are very old and may not represent the current state of Wine.
Selected Test Results (selected in 'Test Results' table below)
What works
Nearly everything, except...
What does not
After reinstalling Wine (moving from 1.0.1 to 1.1.42), multi-engine tournaments began to work correctly, but during the first test tournament of 60 games, one engine did not start properly at the 24-game mark. When I resumed the tournament, the same thing happened again at the 46-game mark. Though the tournament eventually finished, every subsequent tournament with more than two engines finishes the first game fine, but during the start of the second game doesn't get both engines started in a way that they will both move when they are supposed to.
After reinstalling Arena, the same behavior continues. Tournaments of two engines work fine, but using three or more engines, which causes engine unloading and reloading, doesn't get past the first game.
What was not tested
Nothing I can think of.
Additional Comments
I got excited when the tournament was working and posted here immediately, but wish I had run a longer test before concluding everything was fine.
