How to install OSX-Mavericks + Recovery + OSX-Catalina + Windows7/10 and make them all bootable on MacBook Pro 5,5

1. Info: I was running OSX-Catalina and Windows-10 on my MacBook Pro 5,5 with 8 GB RAM and 250 GB SSD. Due to a RAM problem I had to format the hard disk and re-install OS's again. Currently, I have replaced the 250 GB SSD with a 500 GB HDD

2. Info: I have tried multiple times to install OSX-Mavericks + Recovery + OSX-Catalina + Windows-7/10 on to the MacBook but only 2 of the 3 OS's can be made bootable as the other OS partition becomes non bootable. As of now, OSX-Mavericks + Recovery + OSX-Catalina are working fine while Windows-7 says "No Bootable Device - Insert Boot Disk and Press Any Key". Windows-7 was installed through BootCamp on OSX-Mavericks

3. Info: Windows-7 was bootable until installing OSX-Catalina. Windows-7 shows up in "Start-up Disk" on OSX-Mavericks but does not show up while pressing "Option" key during start-up. This happened immediately after installing OSX-Catalina

4. Info: The output of "diskutil list" from OSX-Mavericks is as follows

/dev/disk0
   #:                       TYPE NAME                    SIZE       IDENTIFIER
   0:      GUID_partition_scheme                        *500.1 GB   disk0
   1:                        EFI EFI                     209.7 MB   disk0s1
   2:                  Apple_HFS Mavericks               43.9 GB    disk0s2
   3:                 Apple_Boot Recovery HD             650.0 MB   disk0s3
   4: 7C3457EF-0000-11AA-AA11-00306543ECAC               379.4 GB   disk0s4
   5:       Microsoft Basic Data BOOTCAMP                76.0 GB    disk0s5

5. Info: The output of "diskutil list" from OSX-Catalina is as follows

/dev/disk0 (internal, physical):
   #:                       TYPE NAME                    SIZE       IDENTIFIER
   0:      GUID_partition_scheme                        *500.1 GB   disk0
   1:                        EFI EFI                     209.7 MB   disk0s1
   2:                  Apple_HFS Mavericks               43.9 GB    disk0s2
   3:                 Apple_Boot Recovery HD             650.0 MB   disk0s3
   4:                 Apple_APFS Container disk1         379.4 GB   disk0s4
   5:       Microsoft Basic Data BOOTCAMP                76.0 GB    disk0s5

/dev/disk1 (synthesized):
   #:                       TYPE NAME                    SIZE       IDENTIFIER
   0:      APFS Container Scheme -                      +379.4 GB   disk1
                                 Physical Store disk0s4
   1:                APFS Volume Catalina - Data         3.9 GB     disk1s1
   2:                APFS Volume Preboot                 83.7 MB    disk1s2
   3:                APFS Volume Recovery                731.7 MB   disk1s3
   4:                APFS Volume VM                      3.2 GB     disk1s4
   5:                APFS Volume Catalina                11.4 GB    disk1s5

6. Info: The output of “sudo fdisk /dev/disk0” is as follows

Disk: /dev/disk0    geometry: 60801/255/63 [976773168 sectors]
Signature: 0xAA55
         Starting       Ending
 #: id  cyl  hd sec -  cyl  hd sec [     start -       size]
------------------------------------------------------------------------
 1: EE 1023 254  63 - 1023 254  63 [         1 -  976773167] <Unknown ID>
 2: 00    0   0   0 -    0   0   0 [         0 -          0] unused      
 3: 00    0   0   0 -    0   0   0 [         0 -          0] unused      
 4: 00    0   0   0 -    0   0   0 [         0 -          0] unused      

7. Info: The output of “sudo gpt -r show /dev/disk0” is as follows

      start       size  index  contents
          0          1         PMBR
          1          1         Pri GPT header
          2         32         Pri GPT table
         34          6         
         40     409600      1  GPT part - C12A7328-F81F-11D2-BA4B-00A0C93EC93B
     409640   85738984      2  GPT part - 48465300-0000-11AA-AA11-00306543ECAC
   86148624    1269536      3  GPT part - 426F6F74-0000-11AA-AA11-00306543ECAC
   87418160  740917968      4  GPT part - 7C3457EF-0000-11AA-AA11-00306543ECAC
  828336128  148436992      5  GPT part - EBD0A0A2-B9E5-4433-87C0-68B6B72699C7
  976773120         15         
  976773135         32         Sec GPT table
  976773167          1         Sec GPT header

8. Question-1: Why is Windows-7 partition not bootable after I installed OSX-Catalina ?

9. Question-2: How do I flag the Windows-7 partition as bootable using fdisk or gdisk or any other utility ? (Tried using gdisk, but it only provides option to work with "One to Three" partitions, while I have 5)

10. Question-3: If the answer to "Question-2" is "Not Possible", then what are the steps to install OSX-Mavericks + Recovery + OSX-Catalina + Windows-10 on MacBook Pro 5,5 (Mid 2009)

Thank you for helping, in advance

Question-1: Why is Windows-7 partition not bootable after I installed OSX-Catalina ?

The output of sudo fdisk /dev/disk0 shows the MBR partition table does not contain the Windows 7 partition. So you are asking why the partition can not boot. Well, the reason is because the partition does not exist in the MBR partition table.

Question-2: How do I flag the Windows-7 partition as bootable using fdisk or gdisk or any other utility ? (Tried using gdisk, but it only provides option to work with "One to Three" partitions, while I have 5)

You can use gdisk and omit the 4th partition in the GPT when copying the table entries to the MBR partition table. The interactive commands to enter into gdisk are given below.

r
h
2 3 5
y
af
n
ab
n
07
y
w
y

Below are a few comments.

• The changes made by gdisk may be changed by future use of the diskutil command or the Disk Utility application. If so, then you will need reenter the above commands in to gdisk. One possible solution to this problem would be to install Windows as the second partition on the drive. This would require a manual installation of Windows since the Boot Camp Assistant can not do this.

• The installation of Catalina may be detected by Windows 7. If so, you should be able to fix any Windows 7 boot issues created from the Catalina installation by rebuilding the BCD.

• You should be able to run Windows 10 on this Mac. Upgrading from Windows 7 may still be a free. However, I have not verified the free upgrade for at least a year. You should also be able to do a clean install of Windows 10 using the Windows Support Software Apple provides for your Mac.

Update Regarding Windows 10

The Boot Camp Support Software (Windows Support Software) containing Boot Camp Version 4.0 (Build 4033) is the latest containing Windows drivers provided by Apple for your model Mac. An image of the installer is shown below.

According to Apple these drivers can be used with 64 bit BIOS booting Windows 7 on your Mac. While Apple does not provide Windows 10 drivers for your model Mac, usually the Windows 7 drivers can be substituted, when installing 64 bit Windows 10 to BIOS boot. (Note: The setup.exe application, included with Boot Camp Support Software, has to be executed in Windows 7 Compatibility Mode.) Also, note that Apple Software Update and/or Windows Update may provide newer drivers.

There is also this link from Apple to download a BootCampESD.pkg file. This file can be used to install (by default) the WindowsSupport.dmg file to the "/Library/Application Support/BootCamp" directory. The WindowsSupport.dmg file contains the Windows drivers for your Mac.

So far you have stated (in your question and comments) you can BIOS boot from an USB flash drive and the installation of the Boot Camp Support Software 4.0.4033 after upgrading from Windows 7 to Windows 10 does not fix the driver issues. The ability to BIOS boot from an USB flash drive surprises me, since this conflicts with what I have encountered helping others install Windows 10 on Macs similar to yours. You have stated a clean install of Windows 10, followed by the installation of the Boot Camp Support Software 4.0.4033, does fix the driver issues. Which is good to know.