diff --git a/emulators/i386-wine-devel/Makefile.i386 b/emulators/i386-wine-devel/Makefile.i386
index 2044c8ab616a..d3047e773b7f 100644
--- a/emulators/i386-wine-devel/Makefile.i386
+++ b/emulators/i386-wine-devel/Makefile.i386
@@ -14,10 +14,9 @@ PKGDEINSTALL=	${PKGINSTALL}
 
 RUN_DEPENDS=	mesa-dri>0:graphics/mesa-dri
 
-CONFLICTS_INSTALL?=	wine-[0-9]* wine-staging-[0-9]* wine-devel-[0-9]* \
+CONFLICTS_INSTALL?=	wine-[0-9]* wine-staging-[0-9]* \
 			i386-wine-[0-9]* i386-wine-staging-[0-9]*
 
-ACTUAL-PACKAGE-DEPENDS=	${DO_NADA}
 WINELIBDIR=	${PREFIX}/lib32
 CONFIGURE_ARGS+=	--bindir=${PREFIX}/bin32 --libdir=${WINELIBDIR}
 PLIST_REINPLACE+=	winelib
@@ -36,7 +35,7 @@ post-install-script:
 	# Fix pkg-plist references
 	${REINPLACE_CMD} -e 's!lib/!lib32/!g' ${TMPPLIST}
 	# Install bounce script to access the 32-bit executables
-	${INSTALL_SCRIPT} ${SLAVEDIR}/files/binbounce ${STAGEDIR}${PREFIX}/bin/wine
+	${INSTALL_SCRIPT} ${SLAVEDIR}/files/${BINBOUNCE} ${STAGEDIR}${PREFIX}/bin/wine
 	for i in `${GREP} ^bin ${TMPPLIST} | ${XARGS} -n1 basename` ; do \
 		[ "$${i}" = "wine" ] || ${LN} -f ${STAGEDIR}${PREFIX}/bin/wine ${STAGEDIR}${PREFIX}/bin/$${i} ; \
 		${ECHO_CMD} bin32/$${i} >> ${TMPPLIST} ; \
@@ -77,3 +76,12 @@ post-install-script:
 	${ECHO_CMD} ${DATADIR:S|$(PREFIX)/||}/patch-nvidia.sh >> ${TMPPLIST}
 
 .include "${MASTERDIR}/Makefile"
+
+.if ${PORT_OPTIONS:MWOW64}
+ACTUAL-PACKAGE-DEPENDS=	${ECHO_CMD} "\"wine-devel\": {origin: \"emulators/wine-devel\", version: \"${PKGVERSION}\"}"
+BINBOUNCE=		binbounce.wow64
+.else
+CONFLICTS_INSTALL+=	wine-devel-[0-9]*
+ACTUAL-PACKAGE-DEPENDS=	${DO_NADA}
+BINBOUNCE=		binbounce
+.endif
diff --git a/emulators/i386-wine-devel/files/binbounce.wow64 b/emulators/i386-wine-devel/files/binbounce.wow64
new file mode 100644
index 000000000000..3ea3af7e7158
--- /dev/null
+++ b/emulators/i386-wine-devel/files/binbounce.wow64
@@ -0,0 +1,25 @@
+#!/bin/sh
+
+TARGET="`realpath $0`"
+
+LOCALBASE=${TARGET%/*}/..
+BINNAME=${TARGET##*/}
+
+if [ -z "$__BINBOUNCE_BOOTSTRAP" ]
+then
+  export LIBGL_DRIVERS_PATH=$LOCALBASE/lib32/dri
+  export LD_32_LIBRARY_PATH="$LOCALBASE/lib32":"$LOCALBASE/lib32/wine":"$LD_32_LIBRARY_PATH":/usr/lib32
+  export LD_32_LIBRARY_PATH_RPATH=y
+  export PATH="$LOCALBASE/bin32":"$PATH"
+  export __BINBOUNCE_BOOTSTRAP="1"
+
+  WINE32_VERSION=`$LOCALBASE/bin32/wine --version`
+  WINE64_VERSION=`wine64 --version`
+  if [ "$WINE32_VERSION" != "$WINE64_VERSION" ]
+  then
+    echo "Please, make sure that wine [$WINE32_VERSION] and wine64 [$WINE64_VERSION] versions match each other."
+    exit 1
+  fi
+fi
+
+exec "$LOCALBASE/bin32/$BINNAME" "$@"
diff --git a/emulators/wine-devel/Makefile b/emulators/wine-devel/Makefile
index 09bd72019831..8747bf1a0c7c 100644
--- a/emulators/wine-devel/Makefile
+++ b/emulators/wine-devel/Makefile
@@ -3,7 +3,7 @@
 
 PORTNAME=	wine
 DISTVERSION=	4.21
-PORTEPOCH=	1
+PORTEPOCH=	2
 CATEGORIES=	emulators
 MASTER_SITES=	SF/${PORTNAME}/Source \
 		http://mirrors.ibiblio.org/wine/source/4.x/
@@ -27,7 +27,7 @@ LIB_DEPENDS=	libFAudio.so:audio/faudio \
 USES=		bison desktop-file-utils gmake localbase shebangfix tar:xz xorg
 
 CONFLICTS_INSTALL=	wine-[0-9]* wine-staging-[0-9]* i386-wine-[0-9]* \
-			i386-wine-staging-[0-9]* i386-wine-devel-[0-9]*
+			i386-wine-staging-[0-9]*
 
 GNU_CONFIGURE=	yes
 CONFIGURE_ARGS+=--verbose \
@@ -55,12 +55,14 @@ SHEBANG_FILES=	tools/make_requests tools/winemaker/winemaker \
 
 SUB_FILES=	pkg-message
 
-PORTDATA=	l_intl.nls wine.inf
-
-OPTIONS_DEFINE=	CUPS DOCS DOSBOX GCC GNUTLS HAL LDAP LIBXSLT MPG123 OPENAL STAGING V4L VKD3D VULKAN WINEMAKER X11 GECKO MONO
+OPTIONS_DEFINE=	CUPS DOCS DOSBOX GCC GNUTLS HAL LDAP LIBXSLT MPG123 OPENAL STAGING V4L VKD3D VULKAN WINEMAKER X11 GECKO MONO WOW64
 OPTIONS_DEFAULT=GCC GNUTLS X11
 OPTIONS_SUB=	yes
 
+.if !defined(WINE_CROSS_BUILD)
+OPTIONS_EXCLUDE_i386=WOW64
+.endif
+
 DOSBOX_DESC=	Use DOSBox to run MS-DOS programs
 LIBXSLT_DESC=	Use libxslt (only used by msxml3.dll)
 VKD3D_DESC=	Direct3D 12 support via Vulkan
@@ -68,6 +70,7 @@ VULKAN_DESC=	Vulkan API support
 WINEMAKER_DESC=	Fully support winemaker (requires Perl)
 GECKO_DESC=	Bundle Gecko MSI package for Wine
 MONO_DESC=	Bundle Mono MSI package for Wine
+WOW64_DESC=	Allow simultaneous installation of 32- and 64-bit Wine
 
 CUPS_CONFIGURE_WITH=	cups
 CUPS_LIB_DEPENDS=	libcups.so:print/cups
@@ -122,6 +125,14 @@ X11_LIB_DEPENDS=	libfontconfig.so:x11-fonts/fontconfig \
 
 .include <bsd.port.pre.mk>
 
+.if empty(PORT_OPTIONS:MWOW64) || ${ARCH} == amd64
+PORTDATA=	l_intl.nls wine.inf
+.endif
+
+.if empty(PORT_OPTIONS:MWOW64)
+CONFLICTS_INSTALL+=	i386-wine-devel-[0-9]*
+.endif
+
 .if ${ARCH} == amd64
 # Wine is composed of three parts:
 #  - wine (aka this port) is the 32-bit component and runs 32-bit programs (on FreeBSD/i386)
@@ -136,13 +147,6 @@ X11_LIB_DEPENDS=	libfontconfig.so:x11-fonts/fontconfig \
 # --libdir is required since Wine defaults to "${PREFIX}/lib64" on amd64.
 CONFIGURE_ARGS+=	--enable-win64 --libdir=${PREFIX}/lib
 PLIST_SUB+=		WINE32="@comment " WINE64=""
-
-# Wine assumes a WoW64 package is available, however WoW64 is not yet
-# available on FreeBSD. Also fix the desktop file.
-post-patch:
-	${REINPLACE_CMD} 's|/wine|/wine64|g' ${WRKSRC}/tools/wineapploader.in
-	${REINPLACE_CMD} '/Exec/s|wine|wine64|g' ${WRKSRC}/loader/wine.desktop
-
 .else
 PLIST_SUB+=		WINE32="" WINE64="@comment "
 .endif
@@ -175,6 +179,21 @@ post-install:
 .endfor
 	${INSTALL_DATA} ${WRKSRC}/programs/winedbg/README ${STAGEDIR}${DOCSDIR}/README.winedbg
 	${INSTALL_DATA} ${WRKSRC}/tools/winedump/README ${STAGEDIR}${DOCSDIR}/README.winedump
+.if ${ARCH} == i386 && ${PORT_OPTIONS:MWOW64}
+	for i in `${GREP} ^bin ${TMPPLIST} | ${XARGS} -n1 basename` ; do \
+		[ "$${i}" = "wine" ] || ${RM} ${STAGEDIR}${PREFIX}/bin/$${i} ${STAGEDIR}${PREFIX}/bin32/$${i} ; \
+	done
+	${RM} -r ${STAGEDIR}${PREFIX}/include/wine
+	${RM} -r ${STAGEDIR}${PREFIX}/man
+	${RM} -r ${STAGEDIR}${PREFIX}/share/wine/fonts
+	${RM} -r ${STAGEDIR}${PREFIX}/share/wine/gecko
+	${RM} -r ${STAGEDIR}${PREFIX}/share/wine/mono
+	${RM} -r ${STAGEDIR}${DOCSDIR}
+	${RM} ${STAGEDIR}${PREFIX}/share/applications/wine.desktop
+	${RM} ${STAGEDIR}${PREFIX}/share/wine/*.inf
+	${RM} ${STAGEDIR}${PREFIX}/share/wine/*.nls
+	${REINPLACE_CMD} -n -E -e "/^(@|bin\/wine$$|lib\/)/p" ${TMPPLIST}
+.endif
 
 check-wine-devel-vs-staging:
 	@${GREP} %%STAGING%% pkg-plist | while read f; do \