diff --git a/.circle/Makefile b/.circle/Makefile
index f7e2407f..92d5980e 100644
--- a/.circle/Makefile
+++ b/.circle/Makefile
@@ -283,7 +283,7 @@ requirements: virtualenv .clone_st2_repo .install-runners
 	@echo
 	@echo "==================== requirements ===================="
 	@echo
-	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --upgrade "pip>=9.0,<9.1"
+	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --upgrade "pip==20.0.2"
 	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --cache-dir $(HOME)/.pip-cache -q -r $(CI_DIR)/.circle/requirements-dev.txt
 	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --cache-dir $(HOME)/.pip-cache -q -r $(CI_DIR)/.circle/requirements-pack-tests.txt
 
@@ -292,7 +292,7 @@ requirements-ci:
 	@echo
 	@echo "==================== requirements-ci ===================="
 	@echo
-	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --upgrade "pip>=9.0,<9.1"
+	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --upgrade "pip==20.0.2"
 	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --cache-dir $(HOME)/.pip-cache -q -r $(CI_DIR)/.circle/requirements-dev.txt
 	. $(VIRTUALENV_DIR)/bin/activate && $(VIRTUALENV_DIR)/bin/pip install --cache-dir $(HOME)/.pip-cache -q -r $(CI_DIR)/.circle/requirements-pack-tests.txt
 
diff --git a/.circle/dependencies b/.circle/dependencies
index 19a3f0e9..72a56448 100755
--- a/.circle/dependencies
+++ b/.circle/dependencies
@@ -38,9 +38,12 @@ sudo apt-get -y install libldap2-dev libsasl2-dev
 # Hit github's API to keep the PAT active (without failing if it's not)
 (GH_TOKEN=${MACHINE_PASSWORD} gh repo view | head -n2) || true
 
-sudo pip install -U "pip>=9.0,<9.1" setuptools virtualenv
+# This should track the pinned version of pip in st2's Makefile
+# Please sync this version with .circle/Makefile and .circleci/config.yml
+PIP_VERSION="20.0.2"
 
-virtualenv ~/virtualenv
+sudo pip install -U "pip==${PIP_VERSION}" setuptools virtualenv
+virtualenv --pip "${PIP_VERSION}" ~/virtualenv
 source ~/virtualenv/bin/activate
 
 # Install StackStorm requirements
diff --git a/.circleci/config.yml b/.circleci/config.yml
index 86ec8514..2344f6aa 100755
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -21,7 +21,7 @@ jobs:
           name: Download and Install Dependencies
           command: |
             git clone --depth 1 --single-branch --branch "${LINT_CONFIGS_BRANCH:-master}" https://github.com/StackStorm/lint-configs.git ~/ci/lint-configs
-            sudo pip install -U "pip>=9.0,<9.1" setuptools virtualenv pyyaml
+            sudo pip install -U "pip==20.0.2" setuptools virtualenv pyyaml
             virtualenv ~/virtualenv
             ~/virtualenv/bin/pip install flake8 pylint pyyaml requests
       - save_cache: