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From what I have found across the internet while trying to get PCSX2-CE running using Wineskin, many people have had a lot of difficulty getting it working. I myself could not make Wineskin work and honestly, you are unlikely to get any help using wineskin here due to the infrequency of replies and lack of anyone that actually knows what they're doing.
My solution: CrossOver
CrossOver is a PAID wine-based program by a group of people called CodeWeavers. It is much, much easier to use than Wineskin, and still cheaper and easier on your computer than programs such as Bootcamp. Besides they have an educational discount so if you're a student or teacher at any educational level, they'll take 30% off. I suggest that you start off with the 14-day trial version, however, to make sure you get everything up and running on your machine before paying anything.
How to get PCSX2 working on your Mac using CrossOver:
Step 1: Install CrossOver
Download and install CrossOver onto your Mac. I recommend that you start out with the free trial version so that you can be sure this method will get PCSX2 working on your machine. This worked for me, but PCSX2 is a finicky beasty.
Get the free trial version here:
https://www.codeweavers.com/products/cro..c/download
Get CrossOver full version here:
https://www.codeweavers.com/store2?utm_e..2Fdownload
*Note:* If you are eligible for the educational pricing, all you have to do is ask them, but you can't get the discount after you purchase the software. Ask for educational pricing by following the link below and sending a message to their sales team. Be sure to include the name of your educational institution and the nature of your affiliation (student, teacher, administrator, etc.)
https://www.codeweavers.com/about/contact-us#sales
Step 2: Download PCSX2 1.0.0 for Windows
Version 1.0.0 is the latest PCSX2 version that works using CrossOver. Get the Standalone Installer here:
http://pcsx2.net/download/category/39-pcsx2-v1-0-0.html
Step 3: Download DirectX 11
DirectX is a software designed by Microsoft that is required by PCSX2 in order to correctly display game video. DirectX is free, and while it comes standard on Windows, you can get it here:
http://getintopc.com/softwares/developme..-download/
Step 4: Install PCSX2 Using CrossOver
-Open CrossOver and select the Install a Windows Application button.
-Under 'Select an Appication to Install' type in 'PCSX2 1.0.0' and double click where it lists 'PCSX2 1.0.0 Unlisted Application' and hit Continue.
-Under 'Select Installer' click 'Choose Installer File' and choose the PCSX2 1.0.0 setup .exe that you downloaded in step 2. Click Continue.
-Under 'Select Bottle' Choose Windows Vista and name the bottle 'PCSX2 1.0.0.' Click Continue. Click Continue.
-Under 'Install and Finish,' click Install.
-A window will pop up prompting you to install PCSX2. Follow its instructions. Change the location for PCSX2 to somewhere that you will be able to find easily. Install C++ when it prompts you. Near the end of the installation process, a window will pop up claiming that dxwebinstall.exe (or dxwesetup.exe) has encountered an error and needs to close. This is okay. Just close the error window, and allow PCSX2 to finish the installation.
-After PCSX2 is installed, close the installer window and allow CrossOver to finish. Click 'Done.'
-Go to the location where you chose to install PCSX2 1.0.0. Open the PCSX2 1.0.0 folder and within it create a new folder called 'bios.' Place your legally obtained bios within this folder. For more info on bios and how to get them from your PS2, look elsewhere in this forum.
Step 5: Install DirectX 11 Using Crossover
-Open CrossOver and select the Install a Windows Application button.
-Under 'Select an Application to Install' type in 'DirectX 11' and double click where it lists 'DirectX 11 Unlisted Application' and hit Continue. Do not install DirectX 9 or any of the other Direct X applications that come up when you start to type the name.
-Under 'Select Installer' click 'Choose Installer File' and choose the Getintopc DirectX 11 .exe file that you downloaded in Step 3. Click Continue.
-Under 'Select Bottle' Choose the bottle you made in Step 4, 'PCSX2 1.0.0.' If you don't install DirectX and PCSX2 within the same bottle, your PCSX2 will not have video and only audio will play when you run an ISO. Click Continue.
-Under 'Install and Finish,' click Install.
-A window will pop up prompting you to install DirectX. Follow its instructions.
-After DirectX is installed, close the installer window and allow CrossOver to finish. Click 'Done.'
Step 6: Open PCSX2 through CrossOver
-Open Crossover and open the PCSX2 app located within your PCSX2 bottle.
-Configure PCSX2 1.0.0 using the Official Guide Video that you can find here:
https://www.youtube.com/watch?v=plo8rMytBNg
You are now ready to play your legally obtained ISO's. Happy Gaming!
*Note:* I will be recieving email notifications of any comments posted to this thread, so I should be able to respond to any questions you may have reguarding PCSX2 via CrossOver.

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With over 13,000 Windows programs in compatibility database, the app can run the Windows software you need at home, in the office or at school. The tool runs popular Windows accounting software like Quicken; business and office software like Microsoft Office; lifestyle and hobby software like RootsMagic and gaming software like Steam for Windows.
Check out What Runs database to learn what Windows software customers are using with this app , and then download 14-day, fully-functional trial of Cross Over Mac and see the magic of the app for yourself.
Note: 14 days trial version.