diff --git a/tools/dockerfile/distribtest/python_dev_centos7_x64/Dockerfile b/tools/dockerfile/distribtest/python_dev_centos7_x64/Dockerfile
index 18e3c7b05c6..df5ca6489db 100644
--- a/tools/dockerfile/distribtest/python_dev_centos7_x64/Dockerfile
+++ b/tools/dockerfile/distribtest/python_dev_centos7_x64/Dockerfile
@@ -18,7 +18,7 @@ RUN yum install -y python
 RUN yum install -y python-devel
 RUN yum install -y epel-release
 RUN yum install -y python-pip
-RUN pip install --upgrade pip
+RUN pip install --upgrade pip==19.3.1
 RUN pip install -U virtualenv
 
 # The default gcc of CentOS 7 is gcc 4.8 which is older than gcc 4.9,
diff --git a/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh b/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh
index 5a88b9f8073..4c9dc7a0c44 100755
--- a/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh
+++ b/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh
@@ -25,7 +25,7 @@ cd /var/local/git/grpc
 VIRTUAL_ENV=$(mktemp -d)
 virtualenv "$VIRTUAL_ENV"
 PYTHON="$VIRTUAL_ENV"/bin/python
-"$PYTHON" -m pip install --upgrade pip
+"$PYTHON" -m pip install --upgrade pip==19.3.1
 "$PYTHON" -m pip install --upgrade grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.
diff --git a/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh b/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh
index 533a874844b..e02690d26f4 100755
--- a/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh
+++ b/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh
@@ -25,7 +25,7 @@ cd /var/local/git/grpc
 VIRTUAL_ENV=$(mktemp -d)
 virtualenv "$VIRTUAL_ENV"
 PYTHON="$VIRTUAL_ENV"/bin/python
-"$PYTHON" -m pip install --upgrade pip
+"$PYTHON" -m pip install --upgrade pip==19.3.1
 "$PYTHON" -m pip install --upgrade grpcio grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.
diff --git a/tools/internal_ci/linux/grpc_xds_csharp_test_in_docker.sh b/tools/internal_ci/linux/grpc_xds_csharp_test_in_docker.sh
index b8de27fbeb5..5ed7f2b6edb 100755
--- a/tools/internal_ci/linux/grpc_xds_csharp_test_in_docker.sh
+++ b/tools/internal_ci/linux/grpc_xds_csharp_test_in_docker.sh
@@ -25,7 +25,7 @@ cd /var/local/git/grpc
 VIRTUAL_ENV=$(mktemp -d)
 virtualenv "$VIRTUAL_ENV"
 PYTHON="$VIRTUAL_ENV"/bin/python
-"$PYTHON" -m pip install --upgrade pip
+"$PYTHON" -m pip install --upgrade pip==19.3.1
 "$PYTHON" -m pip install --upgrade grpcio grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.
diff --git a/tools/internal_ci/linux/grpc_xds_php_test_in_docker.sh b/tools/internal_ci/linux/grpc_xds_php_test_in_docker.sh
index 592655dc146..57b6ff6f50e 100755
--- a/tools/internal_ci/linux/grpc_xds_php_test_in_docker.sh
+++ b/tools/internal_ci/linux/grpc_xds_php_test_in_docker.sh
@@ -25,7 +25,7 @@ cd /var/local/git/grpc
 VIRTUAL_ENV=$(mktemp -d)
 virtualenv "$VIRTUAL_ENV"
 PYTHON="$VIRTUAL_ENV"/bin/python
-"$PYTHON" -m pip install --upgrade pip
+"$PYTHON" -m pip install --upgrade pip==19.3.1
 "$PYTHON" -m pip install --upgrade grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.
diff --git a/tools/internal_ci/linux/grpc_xds_ruby_test_in_docker.sh b/tools/internal_ci/linux/grpc_xds_ruby_test_in_docker.sh
index 8cea723fe15..27e8943b4d5 100755
--- a/tools/internal_ci/linux/grpc_xds_ruby_test_in_docker.sh
+++ b/tools/internal_ci/linux/grpc_xds_ruby_test_in_docker.sh
@@ -25,7 +25,7 @@ cd /var/local/git/grpc
 VIRTUAL_ENV=$(mktemp -d)
 virtualenv "$VIRTUAL_ENV"
 PYTHON="$VIRTUAL_ENV"/bin/python
-"$PYTHON" -m pip install --upgrade pip
+"$PYTHON" -m pip install --upgrade pip==19.3.1
 "$PYTHON" -m pip install --upgrade grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.
diff --git a/tools/run_tests/artifacts/build_package_python.sh b/tools/run_tests/artifacts/build_package_python.sh
index 35c78e9a93e..65f694472f1 100755
--- a/tools/run_tests/artifacts/build_package_python.sh
+++ b/tools/run_tests/artifacts/build_package_python.sh
@@ -24,7 +24,7 @@ mkdir -p artifacts/
 cp -r "${EXTERNAL_GIT_ROOT}"/input_artifacts/python_*/* artifacts/ || true
 
 apt-get install -y python-pip
-python -m pip install -U pip
+python -m pip install -U pip==19.3.1
 python -m pip install -U wheel
 
 strip_binary_wheel() {