diff --git a/README.md b/README.md
index bb23a28..aeafcf4 100644
--- a/README.md
+++ b/README.md
@@ -34,7 +34,7 @@ Install the package and include `pip_version` in your tox.ini
 
 ```tox
 [testenv]
-pip_version = 19.0.1
+pip_version = pip==19.0.1
 ```
 
 Or, set the `TOX_PIP_VERSION` environment variable,
@@ -44,7 +44,7 @@ export TOX_PIP_VERSION=18.1
 tox
 ```
 
-The plugin will install that specific pip into the tox-created virtualenv,
+The plugin will install that version of pip into the tox-created virtualenv,
 just after tox creates the virtualenv, but before dependencies are installed.
 
 The `pip_version` within tox.ini, if present, is always used over the
@@ -53,6 +53,21 @@ environment variable.
 If neither `pip_version` or `TOX_PIP_VERSION` is present, the plugin does
 nothing.
 
+### Version Sets
+
+Version sets/ranges are supported, enabling installation of a version of pip
+matching a set of specifiers. There are two basic formats: a plain version
+number, or the package name with optional [PEP440-compatible](
+https://www.python.org/dev/peps/pep-0440/#version-specifiers) version
+specifiers.
+
+| tox.ini                      | effective pip command        |
+| ---------------------------- | ---------------------------- |
+| `pip_version = 19.0`         | `pip install -U pip==19.0`   |
+| `pip_version = pip==19.0`    | `pip install -U pip==19.0`   |
+| `pip_version = pip>=19.0`    | `pip install -U pip>=19.0`   |
+| `pip_version = pip!=19,>18`  | `pip install -U pip!=19,>18` |
+| `pip_version = pip`          | `pip install -U pip`         |
 
 ### Tests
 
diff --git a/dev-requirements.txt b/dev-requirements.txt
index 7f6c649..553d581 100644
--- a/dev-requirements.txt
+++ b/dev-requirements.txt
@@ -1,6 +1,7 @@
 backports.tempfile
 bumpversion
 flake8
+packaging
 pytest
 pytest-xdist
 readme_renderer[md]
diff --git a/tests/check-pip-version.py b/tests/check-pip-version.py
new file mode 100644
index 0000000..89ac340
--- /dev/null
+++ b/tests/check-pip-version.py
@@ -0,0 +1,29 @@
+import subprocess
+import sys
+
+from packaging.version import Version
+from packaging.specifiers import SpecifierSet
+
+VERSION_RANGE_OPERATORS = ('==', '!=', '<', '<=', '>', '>=', '~=', '===')
+
+
+def to_specifer_set(raw_version):
+    if any(raw_version.startswith(op) for op in VERSION_RANGE_OPERATORS):
+        return SpecifierSet(raw_version)
+    return SpecifierSet('==%s' % raw_version)
+
+
+def main():
+    expected_set = to_specifer_set(sys.argv[1])
+    raw_pip_version = subprocess.check_output(["pip", "--version"]).decode()
+    actual_version = Version(raw_pip_version.split(' ')[1])
+    if actual_version not in expected_set:
+        print("FAIL: version '%s' not in set '%s'"
+              % (actual_version, expected_set))
+        return 1
+    print("PASS: version '%s' is in set '%s'" % (actual_version, expected_set))
+    return 0
+
+
+if __name__ == '__main__':
+    sys.exit(main())
diff --git a/tests/check-pip-version.sh b/tests/check-pip-version.sh
deleted file mode 100755
index 4f95821..0000000
--- a/tests/check-pip-version.sh
+++ /dev/null
@@ -1,11 +0,0 @@
-#!/bin/bash -x
-
-EXPECTED_PIP_VERSION="${1?Need expected pip version}"
-PIP_VERSION_OUTPUT=`pip --version`
-
-if [[ "$PIP_VERSION_OUTPUT" == *"$EXPECTED_PIP_VERSION"* ]]; then
-    exit 0
-fi
-
-echo "Expected version ${EXPECTED_PIP_VERSION}, found ${PIP_VERSION_OUTPUT}"
-exit 1
diff --git a/tests/test-env-inheritance/tox.ini b/tests/test-env-inheritance/tox.ini
index 4004513..75d8fc4 100644
--- a/tests/test-env-inheritance/tox.ini
+++ b/tests/test-env-inheritance/tox.ini
@@ -6,12 +6,12 @@ skipsdist = True
 
 [testenv]
 pip_version = 10.0.1
-whitelist_externals = bash
-commands = bash -c '../check-pip-version.sh 10.0.1'
+deps = packaging
+commands = python ../check-pip-version.py 10.0.1
 
 [testenv:env1]
-commands = bash -c '../check-pip-version.sh 10.0.1'
+commands = python ../check-pip-version.py 10.0.1
 
 [testenv:env2]
 pip_version = 18.1
-commands = bash -c '../check-pip-version.sh 18.1'
+commands = python ../check-pip-version.py 18.1
diff --git a/tests/test-environment-variable/tox.ini b/tests/test-environment-variable/tox.ini
index 930065b..bde7b15 100644
--- a/tests/test-environment-variable/tox.ini
+++ b/tests/test-environment-variable/tox.ini
@@ -7,16 +7,16 @@ skipsdist = True
 
 [testenv]
 # 18.1 comes from the TOX_PIP_VERSION env var
-whitelist_externals = bash
-commands = bash -c '../check-pip-version.sh 18.1'
+deps = packaging
+commands = python ../check-pip-version.py 18.1
 
 [testenv:env1]
 # Check that setenv overrides an externally set env var
 setenv =
     TOX_PIP_VERSION = 10.0.1
-commands = bash -c '../check-pip-version.sh 10.0.1'
+commands = python ../check-pip-version.py 10.0.1
 
 [testenv:env2]
 # Check that pip_version wins over env vars
 pip_version = 19.0.1
-commands = bash -c '../check-pip-version.sh 19.0.1'
+commands = python ../check-pip-version.py 19.0.1
diff --git a/tests/test-two-envs/tox.ini b/tests/test-two-envs/tox.ini
index 82c11ae..2e75111 100644
--- a/tests/test-two-envs/tox.ini
+++ b/tests/test-two-envs/tox.ini
@@ -5,12 +5,12 @@ minversion = 2.0
 skipsdist = True
 
 [testenv]
-whitelist_externals = bash
+deps = packaging
 
 [testenv:pip18_1]
 pip_version = 18.1
-commands = bash -c '../check-pip-version.sh 18.1'
+commands = python ../check-pip-version.py 18.1
 
 [testenv:pip19_0_1]
 pip_version = 19.0.1
-commands = bash -c '../check-pip-version.sh 19.0.1'
+commands = python ../check-pip-version.py 19.0.1
diff --git a/tests/test-version-specifiers/tox.ini b/tests/test-version-specifiers/tox.ini
new file mode 100644
index 0000000..a382d7d
--- /dev/null
+++ b/tests/test-version-specifiers/tox.ini
@@ -0,0 +1,44 @@
+# Verify we can use version ranges
+[tox]
+envlist = equal, not_equal, lesser, greater, lesser_eq, greater_eq, tilde_eq, combo, latest
+minversion = 2.0
+skipsdist = True
+
+[testenv]
+deps = packaging
+
+[testenv:equal]
+pip_version = pip==18.1
+commands = python ../check-pip-version.py 18.1
+
+[testenv:not_equal]
+pip_version = pip!=19.0
+commands = python ../check-pip-version.py '!=19.0'
+
+[testenv:lesser]
+pip_version = pip<19.0
+commands = python ../check-pip-version.py '<19.0'
+
+[testenv:greater]
+pip_version = pip>19.0
+commands = python ../check-pip-version.py '>19.0'
+
+[testenv:lesser_eq]
+pip_version = pip<=19.0
+commands = python ../check-pip-version.py '<=19.0'
+
+[testenv:greater_eq]
+pip_version = pip>=19.0
+commands = python ../check-pip-version.py '>=19.0'
+
+[testenv:tilde_eq]
+pip_version = pip~=19.0
+commands = python ../check-pip-version.py '~=19.0'
+
+[testenv:combo]
+pip_version = pip!=19.0,<19.1,>10.0
+commands = python ../check-pip-version.py '!=19.0,<19.1,>10.0'
+
+[testenv:latest]
+pip_version = pip
+commands = python ../check-pip-version.py '>=19.1.1'
diff --git a/tests/test.py b/tests/test.py
index 341decc..0118074 100644
--- a/tests/test.py
+++ b/tests/test.py
@@ -3,13 +3,13 @@
 import subprocess
 import sys
 
+import pytest
+
 if sys.version_info.major == 2:
     from backports import tempfile
 else:
     import tempfile
 
-import pytest
-
 HERE = os.path.realpath(os.path.dirname(__file__))
 PACKAGE_DIR = os.path.realpath(os.path.join(HERE, '..'))
 
@@ -34,6 +34,9 @@
     "test-environment-variable": {
         "env": {"TOX_PIP_VERSION": "18.1"},
     },
+    "test-version-specifiers": {
+        "env": {},
+    }
 }
 
 PYTEST_PARAMETERS = sorted(itertools.product(TOX_VERSIONS, CASES))
diff --git a/tox.ini b/tox.ini
index 8b1841a..5885fd6 100644
--- a/tox.ini
+++ b/tox.ini
@@ -6,4 +6,4 @@ skipsdist = True
 
 [testenv:flake8]
 deps = flake8
-commands = flake8 ./tox_pip_version
+commands = flake8 ./tox_pip_version ./tests
diff --git a/tox_pip_version/hooks.py b/tox_pip_version/hooks.py
index adc28db..f1fc7b9 100644
--- a/tox_pip_version/hooks.py
+++ b/tox_pip_version/hooks.py
@@ -23,6 +23,15 @@ def _testenv_create(venv, action):
     tox_testenv_create(venv, action)
 
 
+def get_pip_package_version(pip_version):
+    pip_version = pip_version.lower().strip()
+    # tox.ini: pip_version = pip==19.0
+    if pip_version.startswith('pip'):
+        return pip_version
+    # tox.ini: pip_version = 19.0
+    return 'pip==%s' % pip_version
+
+
 @tox.hookimpl
 def tox_configure(config):
     for env, envconfig in config.envconfigs.items():
@@ -53,10 +62,11 @@ def tox_testenv_create(venv, action):
     # Use `pip_version` in tox.ini over the environment variable
     pip_version = PER_ENV_PIP_VERSIONS.get(venvname, tox_pip_version_from_env)
     if pip_version:
+        package = get_pip_package_version(pip_version)
+
         # Is there a way to output this better? Genuine tox commands show up
         # colorized (as bold white text)...
-        print("%s: pip_version = %s" % (venvname, pip_version))
-        package = "pip==%s" % pip_version
+        print("%s: pip_version is %s" % (venvname, package))
 
         # "private" _install method - unstable interface?
         venv._install([package], extraopts=["-U"], action=action)