diff --git a/.appveyor.yml b/.appveyor.yml
index c83b66cec41..c623593a0bc 100644
--- a/.appveyor.yml
+++ b/.appveyor.yml
@@ -13,7 +13,7 @@ install:
   # Ensure the Git Submoduldes have been pulled down too
   - git submodule update --init --recursive
 
-  - "tools/build.cmd %PYTHON%\\python.exe -m pip install -U pip wheel setuptools"
+  - "tools/build.cmd %PYTHON%\\python.exe -m pip install -U 'pip<19' wheel setuptools"
   - "tools/build.cmd %PYTHON%\\python.exe -m pip install -r requirements/cython.txt"
   - "tools/build.cmd %PYTHON%\\python.exe -m pip install -r requirements/ci.txt"
 
diff --git a/.travis.yml b/.travis.yml
index 2666be5ea12..b38cb938ab0 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -16,7 +16,7 @@ python:
 - &pypy3 pypy3.5
 
 install:
-- &upgrade_python_toolset pip install --upgrade pip wheel setuptools
+- &upgrade_python_toolset pip install --upgrade 'pip<19' wheel setuptools
 - pip install -r requirements/cython.txt
 - pip install -r requirements/ci.txt
 
diff --git a/Makefile b/Makefile
index 17b299130b2..d7403264ab0 100644
--- a/Makefile
+++ b/Makefile
@@ -110,7 +110,7 @@ doc-spelling:
 	@make -C docs spelling SPHINXOPTS="-W -E"
 
 install:
-	@pip install -U pip
+	@pip install -U 'pip<19'
 	@pip install -Ur requirements/dev.txt
 
 .PHONY: all build flake test vtest cov clean doc