diff --git a/paimon-common/src/main/java/org/apache/paimon/fs/Path.java b/paimon-common/src/main/java/org/apache/paimon/fs/Path.java
index 3cfeac5b6de4..8a0a9f2ae63f 100644
--- a/paimon-common/src/main/java/org/apache/paimon/fs/Path.java
+++ b/paimon-common/src/main/java/org/apache/paimon/fs/Path.java
@@ -115,6 +115,9 @@ public Path(Path parent, Path child) {
                 throw new IllegalArgumentException(e);
             }
         }
+        if (WINDOWS && !child.uri.isAbsolute() && !parentUri.toString().endsWith("/")) {
+            child = new Path(SEPARATOR + child);
+        }
         URI resolved = parentUri.resolve(child.uri);
         initialize(
                 resolved.getScheme(),