diff --git a/platforms/defaults_windows.go b/platforms/defaults_windows.go
index cdbc8751c..fd5756516 100644
--- a/platforms/defaults_windows.go
+++ b/platforms/defaults_windows.go
@@ -50,7 +50,10 @@ func (m windowsmatcher) Match(p specs.Platform) bool {
 	match := m.defaultMatcher.Match(p)
 
 	if match && m.OS == "windows" {
-		return strings.HasPrefix(p.OSVersion, m.osVersionPrefix) && m.defaultMatcher.Match(p)
+		if strings.HasPrefix(p.OSVersion, m.osVersionPrefix) {
+			return true
+		}
+		return p.OSVersion == ""
 	}
 
 	return match
diff --git a/platforms/defaults_windows_test.go b/platforms/defaults_windows_test.go
index eea820f35..468438038 100644
--- a/platforms/defaults_windows_test.go
+++ b/platforms/defaults_windows_test.go
@@ -128,7 +128,7 @@ func TestMatchComparerMatch_WCOW(t *testing.T) {
 				Architecture: "amd64",
 				OS:           "windows",
 			},
-			match: false,
+			match: true,
 		},
 		{
 			platform: imagespec.Platform{
@@ -251,11 +251,11 @@ func TestMatchComparerLess(t *testing.T) {
 		{
 			Architecture: "amd64",
 			OS:           "windows",
-			OSVersion:    "10.0.17764.1",
 		},
 		{
 			Architecture: "amd64",
 			OS:           "windows",
+			OSVersion:    "10.0.17764.1",
 		},
 		{
 			Architecture: "amd64",
diff --git a/platforms/platforms_windows_test.go b/platforms/platforms_windows_test.go
index 89f861926..d5f3883f6 100644
--- a/platforms/platforms_windows_test.go
+++ b/platforms/platforms_windows_test.go
@@ -19,9 +19,23 @@ package platforms
 import (
 	"testing"
 
+	specs "github.com/opencontainers/image-spec/specs-go/v1"
 	"github.com/stretchr/testify/require"
 )
 
 func TestNormalize(t *testing.T) {
 	require.Equal(t, DefaultSpec(), Normalize(DefaultSpec()))
 }
+
+func TestFallbackOnOSVersion(t *testing.T) {
+	p := specs.Platform{
+		OS:           "windows",
+		Architecture: "amd64",
+		OSVersion:    "99.99.99.99",
+	}
+
+	other := specs.Platform{OS: p.OS, Architecture: p.Architecture}
+
+	m := NewMatcher(p)
+	require.True(t, m.Match(other))
+}