diff --git a/ubuntu-win64-cross/Dockerfile b/ubuntu-win64-cross/Dockerfile
index 84b4e2ad7a..41d4ca5881 100644
--- a/ubuntu-win64-cross/Dockerfile
+++ b/ubuntu-win64-cross/Dockerfile
@@ -84,6 +84,7 @@ COPY vulkan-headers.mk \
      glib.mk \
      sdl2.mk \
      libsamplerate.mk \
+     libressl.mk \
      ${MXE_PATH}/src/
 
 RUN make \
@@ -96,7 +97,7 @@ RUN make \
         libepoxy \
         pixman \
         libsamplerate \
-        openssl \
+        libressl \
         cmake \
         libslirp \
         sdl2 \
diff --git a/ubuntu-win64-cross/libressl.mk b/ubuntu-win64-cross/libressl.mk
new file mode 100644
index 0000000000..93d409b836
--- /dev/null
+++ b/ubuntu-win64-cross/libressl.mk
@@ -0,0 +1,19 @@
+# This file is part of MXE. See LICENSE.md for licensing information.
+
+PKG             := libressl
+$(PKG)_WEBSITE  := https://www.libressl.org/
+$(PKG)_DESCR    := libressl
+$(PKG)_IGNORE   :=
+$(PKG)_VERSION  := 4.0.0
+$(PKG)_SUBDIR   := libressl-$($(PKG)_VERSION)
+$(PKG)_FILE     := libressl-$($(PKG)_VERSION).tar.gz
+$(PKG)_CHECKSUM := 4d841955f0acc3dfc71d0e3dd35f283af461222350e26843fea9731c0246a1e4
+$(PKG)_URL      := https://github.com/libressl/portable/releases/download/v$($(PKG)_VERSION)/$($(PKG)_FILE)
+$(PKG)_DEPS     := cc
+
+define $(PKG)_BUILD
+    cd '$(BUILD_DIR)' && $(TARGET)-cmake '$(SOURCE_DIR)' \
+        -DVERBOSE=1
+    $(MAKE) -C '$(BUILD_DIR)' -j '$(JOBS)'
+    $(MAKE) -C '$(BUILD_DIR)' -j 1 install
+endef