diff --git a/print/py-fonttools/Makefile b/print/py-fonttools/Makefile
index 0028aeecd8d0a..e566e4383b9b8 100644
--- a/print/py-fonttools/Makefile
+++ b/print/py-fonttools/Makefile
@@ -1,5 +1,5 @@
 PORTNAME=	fonttools
-PORTVERSION=	4.43.1
+PORTVERSION=	4.44.0
 CATEGORIES=	print python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -40,8 +40,8 @@ WOFF_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}brotli>=1.0.1:archivers/py-brotli@${PY_
 
 .include <bsd.port.pre.mk>
 
-.if ${PORT_OPTIONS:UNICODE} && ${PYTHON_REL} < 31200
-RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}unicodedata2>=15.0.0:devel/py-unicodedata2@${PY_FLAVOR}
+.if ${PORT_OPTIONS:UNICODE} && ${PYTHON_REL} < 31299
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}unicodedata2>=15.1.0:devel/py-unicodedata2@${PY_FLAVOR}
 .endif
 
 post-install:
diff --git a/print/py-fonttools/distinfo b/print/py-fonttools/distinfo
index ef9aeec384b9b..b8b453b7ba35f 100644
--- a/print/py-fonttools/distinfo
+++ b/print/py-fonttools/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1696753684
-SHA256 (fonttools-4.43.1.tar.gz) = 17dbc2eeafb38d5d0e865dcce16e313c58265a6d2d20081c435f84dc5a9d8212
-SIZE (fonttools-4.43.1.tar.gz) = 3372820
+TIMESTAMP = 1699774652
+SHA256 (fonttools-4.44.0.tar.gz) = 4e90dd81b6e0d97ebfe52c0d12a17a9ef7f305d6bfbb93081265057d6092f252
+SIZE (fonttools-4.44.0.tar.gz) = 3378114