diff --git a/multimedia/streamlink/Makefile b/multimedia/streamlink/Makefile
index 4d7d52361ae8..c99b75baa3be 100644
--- a/multimedia/streamlink/Makefile
+++ b/multimedia/streamlink/Makefile
@@ -1,51 +1,45 @@
 PORTNAME=	streamlink
-PORTVERSION=	2.1.2
-PORTREVISION=	1
+PORTVERSION=	5.5.1
 CATEGORIES=	multimedia
-MASTER_SITES=	PYPI
+MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	takefu@airport.fm
 COMMENT=	Command-line utility that pipes video streams
 WWW=		https://streamlink.github.io/
 
 LICENSE=	BSD2CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}isodate>0:devel/py-isodate@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pycryptodome>=3.4.3:security/py-pycryptodome@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pysocks>0:net/py-pysocks@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}requests>0:www/py-requests@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}websocket-client>=0.58.0:www/py-websocket-client@${PY_FLAVOR}
-
-TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}backports>0:devel/py-backports@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}country>0:devel/py-country@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}freezegun>0:devel/py-freezegun@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=45.0.0:devel/py-setuptools@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}versioningit>=2.0.0:devel/py-versioningit@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${PY_FLAVOR}
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}certifi>0:security/py-certifi@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}country>0:devel/py-country@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}isodate>0:devel/py-isodate@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}lxml>=4.6.4:devel/py-lxml@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}pycryptodome>=3.4.3:security/py-pycryptodome@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}pysocks>1.5.7:net/py-pysocks@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}requests>2.26.0:www/py-requests@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}websocket-client>=1.2.1:www/py-websocket-client@${PY_FLAVOR}
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}backports>0:devel/py-backports@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}flake8>0:devel/py-flake8@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}freezegun>0:devel/py-freezegun@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR}\
+		${PYTHON_PKGNAMEPREFIX}pytest-asyncio>0:devel/py-pytest-asyncio@${PY_FLAVOR}\
 		${PYTHON_PKGNAMEPREFIX}requests-mock>0:www/py-requests-mock@${PY_FLAVOR}
 
-USES=		python:3.6+
+USES=		python:3.7+
 USE_PYTHON=	autoplist concurrent distutils
-
 NO_ARCH=	yes
-
-OPTIONS_DEFINE=		FFMPEG PYCOUNTRY RTMPDUMP
+OPTIONS_DEFINE=		FFMPEG RTMPDUMP
 OPTIONS_DEFAULT=	FFMPEG RTMPDUMP
-.if !exists(../../textproc/py-iso3166/Makefile)
-OPTIONS_DEFAULT+=	PYCOUNTRY
-.endif
-PYCOUNTRY_DESC=		Use pycountry instead of py-iso-639 and py-iso3166
-
-FFMPEG_RUN_DEPENDS=		ffmpeg:multimedia/ffmpeg
-PYCOUNTRY_RUN_DEPENDS=		${PYTHON_PKGNAMEPREFIX}country>0:devel/py-country@${PY_FLAVOR}
-PYCOUNTRY_RUN_DEPENDS_OFF=	${PYTHON_PKGNAMEPREFIX}iso-639>0:textproc/py-iso-639@${PY_FLAVOR} \
-				${PYTHON_PKGNAMEPREFIX}iso3166>0:textproc/py-iso3166@${PY_FLAVOR}
-PYCOUNTRY_MAKE_ENV=		STREAMLINK_USE_PYCOUNTRY=1
-RTMPDUMP_RUN_DEPENDS=		rtmpdump:multimedia/rtmpdump
+FFMPEG_RUN_DEPENDS=	ffmpeg:multimedia/ffmpeg
+RTMPDUMP_RUN_DEPENDS=	rtmpdump:multimedia/rtmpdump
 
 do-test:	.PHONY
 		cd ${WRKSRC} && ${SETENV} PYTHONPATH=${WRKSRC}/src ${PYTHON_CMD} -u -m pytest -v -ra \
 		|| ${SETENV} PYTHONPATH=${WRKSRC}/src ${PYTHON_CMD} -um unittest discover -v
 
 .include <bsd.port.mk>
diff --git a/multimedia/streamlink/distinfo b/multimedia/streamlink/distinfo
index c4c55e7687b7..e94873500151 100644
--- a/multimedia/streamlink/distinfo
+++ b/multimedia/streamlink/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1621854352
-SHA256 (streamlink-2.1.2.tar.gz) = 5e3be17673ed6b7da359a4636bd1e6961b4e58acb2dd7d219f9aaab377a4c84d
-SIZE (streamlink-2.1.2.tar.gz) = 509287
+TIMESTAMP = 1683693187
+SHA256 (streamlink-5.5.1.tar.gz) = b2b4fe8d6436dbe7bcec78de2d4bb780156388561435b61a1963156e9fc5fbd0
+SIZE (streamlink-5.5.1.tar.gz) = 536064
diff --git a/multimedia/streamlink/pkg-descr b/multimedia/streamlink/pkg-descr
index abc52005701a..260face4bfbf 100644
--- a/multimedia/streamlink/pkg-descr
+++ b/multimedia/streamlink/pkg-descr
@@ -1,10 +1,10 @@
-Streamlink is a command-line utility that pipes video streams from various
+Streamlink is a command-line utility which pipes video streams from various
 services into a video player, such as VLC.
 
-The main purpose of Streamlink is to allow the user to avoid buggy and CPU
-heavy flash plugins but still be able to enjoy various streamed content.
+The main purpose of Streamlink is to avoid resource-heavy and unoptimized
+websites, while still allowing the user to enjoy various streamed content.
 
-There is also an API available for developers who want access to the video
-stream data.
+There is also an API available for developers who want access to the stream
+data.
 
 This project was forked from Livestreamer, which is no longer maintained.