Seems fixed with latest versions:

# dpkg -I test_1.0_all.deb
 new debian package, version 2.0.
 size 2054 bytes: control archive= 447 bytes.
     228 bytes,    10 lines      control
     196 bytes,     3 lines      md5sums
 Package: test
 Version: 1.0
 Architecture: all
 Maintainer: Luca Falavigna <[email protected]>
 Installed-Size: 36
 Depends: dpkg (>= 1.15.8.9) | dpkg (<< 1.15.8.9)
 Section: misc
 Priority: optional
 Description: test
  test package
# gdebi test_1.0_all.deb
Reading package lists... Done
Building dependency tree
Reading state information... Done
Building data structures... Done
Building data structures... Done


test
 test package
Do you want to install the software package? [y/N]:y
Selecting previously deselected package test.
(Reading database ... 22971 files and directories currently installed.)
Unpacking test (from test_1.0_all.deb) ...
Setting up test (1.0) ...

#

** Changed in: gdebi (Ubuntu)
       Status: New => Fix Released

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https://bugs.launchpad.net/bugs/640369

Title:
  gdebi interprets OR as AND in run-time dependencies

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