diff --git a/testfiles/CMakeLists.txt b/testfiles/CMakeLists.txt
index 8983863fa687991e7cec5231039d73a6faf9d844..1ad1ce9d9c2628b75f4fa191f787bb1dc49de02f 100644
--- a/testfiles/CMakeLists.txt
+++ b/testfiles/CMakeLists.txt
@@ -58,6 +58,7 @@ set(TEST_SOURCES
     sp-object-test
     object-set-test
     object-style-test
+    path-boolop-test
     rebase-hrefs-test
     style-elem-test
     style-internal-test
diff --git a/testfiles/src/path-boolop-test.cpp b/testfiles/src/path-boolop-test.cpp
new file mode 100644
index 0000000000000000000000000000000000000000..d2321f544cd853f818088041d4511a7513a5b819
--- /dev/null
+++ b/testfiles/src/path-boolop-test.cpp
@@ -0,0 +1,89 @@
+// SPDX-License-Identifier: GPL-2.0-or-later
+#include <gtest/gtest.h>
+#include <src/path/path-boolop.h>
+#include <src/svg/svg.h>
+#include <2geom/svg-path-writer.h>
+
+class PathBoolopTest : public ::testing::Test
+{
+    public:
+        std::string rectangle_bigger =  "M 0,0 L 0,2 L 2,2 L 2,0 z";
+        std::string rectangle_smaller = "M 0.5,0.5 L 0.5,1.5 L 1.5,1.5 L 1.5,0.5 z";
+        std::string rectangle_outside =  "M 0,1.5 L 0.5,1.5 L 0.5,2.5 L 0,2.5 z";
+        std::string rectangle_outside_union = "M 0,0 L 0,1.5 L 0,2 L 0,2.5 L 0.5,2.5 L 0.5,2 L 2,2 L 2,0 L 0,0 z";
+        Geom::PathVector pvRectangleBigger;
+        Geom::PathVector pvRectangleSmaller;
+        Geom::PathVector pvRectangleOutside;
+        Geom::PathVector pvTargetUnion;
+        Geom::PathVector pvEmpty;
+        PathBoolopTest() {
+            pvRectangleBigger = sp_svg_read_pathv(rectangle_bigger.c_str());
+            pvRectangleSmaller = sp_svg_read_pathv(rectangle_smaller.c_str());
+            pvRectangleOutside = sp_svg_read_pathv(rectangle_outside.c_str());
+            pvTargetUnion = sp_svg_read_pathv(rectangle_outside_union.c_str());
+            pvEmpty = sp_svg_read_pathv("");
+        }
+        void comparePaths(Geom::PathVector result, Geom::PathVector target){
+            Geom::SVGPathWriter wr;
+            wr.feed(result);
+            std::string resultD = wr.str();
+            wr.clear();
+            wr.feed(target);
+            std::string targetD = wr.str();
+            EXPECT_EQ(resultD, targetD);
+            EXPECT_EQ(result, target);
+        }
+};
+
+TEST_F(PathBoolopTest, UnionOutside){
+    // test that the union of two objects where one is outside the other results in a new larger shape
+    Geom::PathVector pvRectangleUnion  = sp_pathvector_boolop(pvRectangleBigger, pvRectangleOutside, bool_op_union, fill_oddEven, fill_oddEven);
+    comparePaths(pvRectangleUnion, pvTargetUnion);
+}
+
+TEST_F(PathBoolopTest, UnionOutsideSwap){
+    // test that the union of two objects where one is outside the other results in a new larger shape, even when the order is reversed
+    Geom::PathVector pvRectangleUnion  = sp_pathvector_boolop(pvRectangleOutside, pvRectangleBigger, bool_op_union, fill_oddEven, fill_oddEven);
+    comparePaths(pvRectangleUnion, pvTargetUnion);
+}
+
+TEST_F(PathBoolopTest, UnionInside){
+    // test that the union of two objects where one is completely inside the other is the larger shape
+    Geom::PathVector pvRectangleUnion  = sp_pathvector_boolop(pvRectangleBigger, pvRectangleSmaller, bool_op_union, fill_oddEven, fill_oddEven);
+    comparePaths(pvRectangleUnion, pvRectangleBigger);
+}
+
+TEST_F(PathBoolopTest, UnionInsideSwap){
+    // test that the union of two objects where one is completely inside the other is the larger shape, even when the order is swapped
+    Geom::PathVector pvRectangleUnion  = sp_pathvector_boolop(pvRectangleSmaller, pvRectangleBigger, bool_op_union, fill_oddEven, fill_oddEven);
+    comparePaths(pvRectangleUnion, pvRectangleBigger);
+}
+
+TEST_F(PathBoolopTest, IntersectionInside){
+    // test that the intersection of two objects where one is completely inside the other is the smaller shape
+    Geom::PathVector pvRectangleIntersection  = sp_pathvector_boolop(pvRectangleBigger, pvRectangleSmaller, bool_op_inters, fill_oddEven, fill_oddEven);
+    comparePaths(pvRectangleIntersection, pvRectangleSmaller);
+}
+
+TEST_F(PathBoolopTest, DifferenceInside){
+    // test that the difference of two objects where one is completely inside the other is an empty path
+    Geom::PathVector pvRectangleDifference  = sp_pathvector_boolop(pvRectangleBigger, pvRectangleSmaller, bool_op_diff, fill_oddEven, fill_oddEven);
+    comparePaths(pvRectangleDifference, pvEmpty);
+}
+
+TEST_F(PathBoolopTest, DifferenceOutside){
+    // test that the difference of two objects where one is completely outside the other is multiple shapes
+    Geom::PathVector pvRectangleDifference = sp_pathvector_boolop(pvRectangleSmaller, pvRectangleBigger, bool_op_diff, fill_oddEven, fill_oddEven);
+    std::string bothPaths = rectangle_bigger + rectangle_smaller;
+    Geom::PathVector pvRectangleSmallerReversed = pvRectangleSmaller;
+    Geom::PathVector pvBothPaths = pvRectangleBigger;
+    
+    pvRectangleSmallerReversed.reverse();
+    for(Geom::Path _path:pvRectangleSmallerReversed){
+        pvBothPaths.push_back(_path);
+    }
+
+    comparePaths(pvRectangleDifference, pvBothPaths);
+}
+
+//
\ No newline at end of file