diff --git a/core/os/os2/path.odin b/core/os/os2/path.odin
index c3effe69e..1d3dca5c9 100644
--- a/core/os/os2/path.odin
+++ b/core/os/os2/path.odin
@@ -771,6 +771,14 @@ scan_chunk :: proc(pattern: string) -> (star: bool, chunk, rest: string) {
 
 @(private="file")
 match_chunk :: proc(chunk, s: string) -> (rest: string, ok: bool, err: Error) {
+	slash_equal :: proc(a, b: u8) -> bool {
+		switch a {
+		case '/':  return b == '/' || b == '\\'
+		case '\\': return b == '/' || b == '\\'
+		case: return a == b
+		}
+	}
+
 	chunk, s := chunk, s
 	for len(chunk) > 0 {
 		if len(s) == 0 {
@@ -831,7 +839,7 @@ match_chunk :: proc(chunk, s: string) -> (rest: string, ok: bool, err: Error) {
 			}
 			fallthrough
 		case:
-			if chunk[0] != s[0] {
+			if !slash_equal(chunk[0], s[0]) {
 				return
 			}
 			s = s[1:]
diff --git a/tests/core/os/os2/path.odin b/tests/core/os/os2/path.odin
index 26cf1c290..a256b3e22 100644
--- a/tests/core/os/os2/path.odin
+++ b/tests/core/os/os2/path.odin
@@ -1,5 +1,6 @@
 package tests_core_os_os2
 
+import    "core:fmt"
 import os "core:os/os2"
 import    "core:log"
 import    "core:testing"
@@ -386,24 +387,62 @@ Glob_Test :: struct {
 glob_tests := []Glob_Test{
 	{
 		pattern = ODIN_ROOT + "tests/core/os/*/*.txt",
-		matches = {},
-		err     = nil,
+		matches = {
+			ODIN_ROOT + "tests/core/os/dir/b.txt",
+		},
+		err     = {},
+	},
+	{
+		pattern = ODIN_ROOT + "tests/core/os/os2/*.odin",
+		matches = {
+			ODIN_ROOT + "tests/core/os/os2/dir.odin",
+			ODIN_ROOT + "tests/core/os/os2/file.odin",
+			ODIN_ROOT + "tests/core/os/os2/path.odin",
+			ODIN_ROOT + "tests/core/os/os2/process.odin",
+		},
+		err     = {},
 	},
 }
 
 @(test)
 test_glob :: proc(t: ^testing.T) {
+	compare_matches :: proc(t: ^testing.T, pattern: string, globbed, expected: []string) {
+		glob_fold   := make([]string, len(globbed), context.temp_allocator)
+		expect_fold := make([]string, len(globbed), context.temp_allocator)
+
+		for glob, i in globbed {
+			// If `glob` returned a path in response to a pattern,
+			// then `match` should consider that path a match, too,
+			// irrespective of `/` versus `\` presence.
+			no_match_msg := fmt.tprintf("Expected os.match(%q, %q) to be `true`, got `false`", pattern, glob)
+			match, _ := os.match(pattern, glob)
+
+			f, _ := strings.replace_all(glob, `\`, `/`, context.temp_allocator)
+			glob_fold[i] = f
+			testing.expect(t, match, no_match_msg)
+		}
+
+		for exp, i in expected {
+			f, _ := strings.replace_all(exp, `\`, `/`, context.temp_allocator)
+			expect_fold[i] = f
+		}
+
+		slice.sort(glob_fold)
+		slice.sort(expect_fold)
+
+		not_equal_msg := fmt.tprintf("Expected os.glob(%q) to return %v, got %v", pattern, glob_fold, expect_fold)
+		testing.expect(t, slice.equal(glob_fold, expect_fold), not_equal_msg)
+	}
+
 	for glob in glob_tests {
-		files, err := os.glob(glob.pattern, context.allocator)
+		globbed, err := os.glob(glob.pattern, context.allocator)
 		defer {
-			for file in files {
+			for file in globbed {
 				delete(file)
 			}
-			delete(files)
+			delete(globbed)
 		}
 		testing.expect_value(t, err, glob.err)
-
-		slice.sort(files)
-		log.infof("files: %v", files)
+		compare_matches(t, glob.pattern, globbed, glob.matches)
 	}
 }
\ No newline at end of file