diff --git a/lib/listen/record.rb b/lib/listen/record.rb
index 144bc058..e6a03959 100644
--- a/lib/listen/record.rb
+++ b/lib/listen/record.rb
@@ -64,7 +64,10 @@ def _sub_tree(rel_path)
         if path == rel_path
           result.merge!(meta)
         else
-          sub_path         = path.sub(%r{\A#{rel_path}/?}, '')
+          parts = path.split(::File::SEPARATOR)
+          next unless parts.include?(rel_path)
+
+          sub_path = (parts - [rel_path]).join(::File::SEPARATOR)
           result[sub_path] = meta
         end
       end
diff --git a/spec/lib/listen/record_spec.rb b/spec/lib/listen/record_spec.rb
index 7d3b2c15..5c4c7e78 100644
--- a/spec/lib/listen/record_spec.rb
+++ b/spec/lib/listen/record_spec.rb
@@ -208,6 +208,29 @@ def record_tree(record)
       end
     end
 
+    context 'when there is a file with the same name as a dir' do
+      subject { record.dir_entries('cypress') }
+
+      before do
+        record.update_file('cypress.json', mtime: 1.1)
+        record.update_file('cypress/README.md', mtime: 1.2)
+        record.update_file('a/b/cypress/d', mtime: 1.3)
+        record.update_file('a/b/c/cypress', mtime: 1.3)
+      end
+      it { should eq('README.md' => { mtime: 1.2 }) }
+    end
+
+    context 'when there is a file with a similar name to a dir' do
+      subject { record.dir_entries('app') }
+
+      before do
+        record.update_file('appspec.yml', mtime: 1.1)
+        record.update_file('app/README.md', mtime: 1.2)
+        record.update_file('spec/app/foo', mtime: 1.3)
+      end
+      it { should eq('README.md' => { mtime: 1.2 }) }
+    end
+
     context 'in subdir /path' do
       subject { record.dir_entries('path') }