diff --git a/lib/gitlab/ci/pipeline/seed/build/cache.rb b/lib/gitlab/ci/pipeline/seed/build/cache.rb
index 7df84afe0f911b3ec127b4f087f1ed9399d7df51..f76683a662349d097212b0be0c4f6f39a791644e 100644
--- a/lib/gitlab/ci/pipeline/seed/build/cache.rb
+++ b/lib/gitlab/ci/pipeline/seed/build/cache.rb
@@ -62,9 +62,10 @@ def cache_key_digest
             end
 
             def hash_of_file_contents
-              return unless files.any?
+              expanded_paths = expand_file_patterns(files)
+              return unless expanded_paths.any?
 
-              blob_references = files.map { |path| [@pipeline.sha, path] }
+              blob_references = expanded_paths.map { |path| [@pipeline.sha, path] }
               content_hashes = @pipeline.project.repository
                 .blobs_at(blob_references, blob_size_limit: 0)
                 .map(&:id)
@@ -90,6 +91,20 @@ def files_commits_files
               @key[:files_commits].to_a.select(&:present?).uniq
             end
 
+            def expand_file_patterns(patterns)
+              @expanded_patterns ||= begin
+                expanded = patterns.flat_map do |pattern|
+                  if pattern.include?('*')
+                    @pipeline.project.repository.search_files_by_wildcard_path(pattern, @pipeline.sha)
+                  else
+                    pattern
+                  end
+                end.compact.uniq
+
+                expanded.first(100)
+              end
+            end
+
             def last_commit_id_for_path(path)
               @pipeline.project.repository.last_commit_id_for_path(@pipeline.sha, path)
             end
diff --git a/spec/lib/gitlab/ci/pipeline/seed/build/cache_spec.rb b/spec/lib/gitlab/ci/pipeline/seed/build/cache_spec.rb
index beee721c20c9c810fc62add33eb0ae0f5bd6e80d..696e999fef7a2007a7e251cfebc0764b9c25c3df 100644
--- a/spec/lib/gitlab/ci/pipeline/seed/build/cache_spec.rb
+++ b/spec/lib/gitlab/ci/pipeline/seed/build/cache_spec.rb
@@ -108,6 +108,20 @@
         end
       end
 
+      context 'with only ./ relative paths' do
+        let(:config) do
+          {
+            key: { files: ['./VERSION'], prefix: 'relative' },
+            paths: ['vendor/ruby']
+          }
+        end
+
+        it 'falls back to default key as relative paths are not supported' do
+          expect(subject[:key]).to eq('relative-default')
+          expect(subject[:paths]).to eq(['vendor/ruby'])
+        end
+      end
+
       context 'with invalid file patterns' do
         where(:files, :expected_prefix) do
           [
@@ -144,6 +158,48 @@
           end
         end
       end
+
+      context 'with wildcard patterns' do
+        let(:config) do
+          {
+            key: { files: ['**/*.rb'], prefix: 'wildcard' },
+            paths: ['vendor/ruby']
+          }
+        end
+
+        it 'expands wildcard patterns and builds cache key from matched files' do
+          expect(subject[:key]).to match(/^wildcard-[a-f0-9]+$/)
+          expect(subject[:paths]).to eq(['vendor/ruby'])
+        end
+      end
+
+      context 'with mixed wildcard and non-wildcard patterns' do
+        let(:config) do
+          {
+            key: { files: ['VERSION', '*.gemspec'], prefix: 'mixed' },
+            paths: ['vendor/ruby']
+          }
+        end
+
+        it 'expands wildcards and includes non-wildcard files' do
+          expect(subject[:key]).to match(/^mixed-[a-f0-9]+$/)
+          expect(subject[:paths]).to eq(['vendor/ruby'])
+        end
+      end
+
+      context 'with wildcard pattern matching no files' do
+        let(:config) do
+          {
+            key: { files: ['**/nonexistent/*.txt'], prefix: 'empty' },
+            paths: ['vendor/ruby']
+          }
+        end
+
+        it 'falls back to default key when no files match' do
+          expect(subject[:key]).to eq('empty-default')
+          expect(subject[:paths]).to eq(['vendor/ruby'])
+        end
+      end
     end
 
     context 'with cache:key:prefix' do