Let me start off by saying Rise of Legends is one of my favorite game. This game is also now very old. It looks like this forum has not been updated recently the lasts posts are from 2009 or older. I have had some luck running this program in Crossover 18.5 for mac. Your mileage may very in your case, but here is how I got it to work. You will see some graphics and audio issues when you play it in crossover. Also this will NOT run on mac OS 10.15 (Catalina) -currently as this is a 32-bit app and I doubt it will be updated here is what I did.
Create a Windows 7 Bottle
You will need these programs Installed in the same bottle
.NET Framework 1.1, 2.0 with SP2, 3.0 with SP2, 3.5 With SP1, 4.0, 4.5, 4.5.2, 4.6.2
Microsoft Visual C++ 2005 SP1, 2012, 2013
Microsoft XML Parser MSXML 3.0, 4.0 SP3, 6.0 SP2
Microsoft Direct X for Pre Windows XP Games & For Modern Games
Hotfix for XP KB954550 V5 Also Hotfix for .NET 3.5 SP1
Microsoft Rich Text Edit 2.0 & 4.1
Install Steam (This will get your various fonts needed for the game)
Install Rise of Legends
Update Rise of Legends to latest version, you can do this by downloading the patches and copying the patched to the Rise of Legends Install Directory inside the bottle and running the updater tool found in the folder. You will need to click through several error messages
Once all of that is installed restart the bottle by going to control panels and simulate reboot. Now launch the game. You will see a message AGP Texture Acceleration. Click OK and the game should launch. As you play the game, particularly the campaign you will see some graphics issues and audio issues around campaign in game dialogue. Turn on the subtitles to get some of the missing game information that is spoken that you can not hear. Also, It is recommended you run this game on a Mac that has a dedicated graphics card. This will greatly improve performance.
Screenshot of error message
Screenshot of game main menu
https://photos.app.goo.gl/jGUMYeLD9aYNHU8W8