diff --git a/src/parser-includes.ts b/src/parser-includes.ts
index cbb3f6aa6..b81b972df 100644
--- a/src/parser-includes.ts
+++ b/src/parser-includes.ts
@@ -11,6 +11,7 @@ import path from "node:path";
 import prettyHrtime from "pretty-hrtime";
 import semver from "semver";
 import {RE2JS} from "re2js";
+import {globbySync} from "globby";
 
 type ParserIncludesInitOptions = {
     argv: Argv;
@@ -147,13 +148,16 @@ export class ParserIncludes {
             } else if (value["project"]) {
                 for (const fileValue of Array.isArray(value["file"]) ? value["file"] : [value["file"]]) {
                     const mergedInputs = {...(value.inputs ?? {}), ...globalInputs};
-                    const fileDoc = await Parser.loadYaml(
-                        `${cwd}/${stateDir}/includes/${gitData.remote.host}/${value["project"]}/${value["ref"] || "HEAD"}/${fileValue}`
-                        , {inputs: mergedInputs}
-                        , expandVariables, writeStreams);
-                    // Expand local includes inside a "project"-like include
-                    fileDoc["include"] = this.expandInnerLocalIncludes(fileDoc["include"], value["project"], value["ref"], opts);
-                    includeDatas = includeDatas.concat(await this.init(fileDoc, opts));
+                    const includeDir = `${cwd}/${stateDir}/includes/${gitData.remote.host}/${value["project"]}/${value["ref"] || "HEAD"}`;
+                    const normalizedFile = fileValue.replace(/^\/+/, "");
+                    const matches = globbySync(normalizedFile, {cwd: includeDir, absolute: true}).sort((a, b) => a.localeCompare(b));
+                    const filePaths = matches.length > 0 ? matches : [`${includeDir}/${normalizedFile}`];
+                    for (const filePath of filePaths) {
+                        const fileDoc = await Parser.loadYaml(filePath, {inputs: mergedInputs}, expandVariables, writeStreams);
+                        // Expand local includes inside a "project"-like include
+                        fileDoc["include"] = this.expandInnerLocalIncludes(fileDoc["include"], value["project"], value["ref"], opts);
+                        includeDatas = includeDatas.concat(await this.init(fileDoc, opts));
+                    }
                 }
             } else if (value["component"]) {
                 const component = componentParseCache.get(index);
@@ -374,7 +378,8 @@ export class ParserIncludes {
 
             if (remote.schema.startsWith("http")) {
                 const ext = "tmp-" + Math.random();
-                await fs.mkdirp(path.dirname(`${cwd}/${target}/${normalizedFile}`));
+                const destDir = path.dirname(`${cwd}/${target}/${normalizedFile}`);
+                await fs.mkdirp(destDir);
                 tmpDir = `${cwd}/${target}.${ext}`;
 
                 const isCommitSha = /^[0-9a-f]{40}$/i.test(ref);
@@ -387,7 +392,7 @@ export class ParserIncludes {
                     `git sparse-checkout set --no-cone ${normalizedFile}`,
                     isCommitSha ? "git checkout FETCH_HEAD" : "git checkout",
                     `cd ${cwd}/${stateDir}`,
-                    `cp ${tmpDir}/${normalizedFile} ${cwd}/${target}/${normalizedFile}`,
+                    `cp ${tmpDir}/${normalizedFile} ${destDir}/`,
                 ], cwd);
             } else {
                 await fs.mkdirp(`${cwd}/${target}`);
diff --git a/tests/test-cases/include-project-file-wildcard/.gitlab-ci.yml b/tests/test-cases/include-project-file-wildcard/.gitlab-ci.yml
new file mode 100644
index 000000000..e820a2eda
--- /dev/null
+++ b/tests/test-cases/include-project-file-wildcard/.gitlab-ci.yml
@@ -0,0 +1,7 @@
+---
+# templates/[bt]*.yml matches both templates/build.yml and templates/test.yml,
+# so the glob expands to more than one file.
+include:
+  - project: components/go
+    ref: main
+    file: templates/[bt]*.yml
diff --git a/tests/test-cases/include-project-file-wildcard/integration.test.ts b/tests/test-cases/include-project-file-wildcard/integration.test.ts
new file mode 100644
index 000000000..39e9ad2a0
--- /dev/null
+++ b/tests/test-cases/include-project-file-wildcard/integration.test.ts
@@ -0,0 +1,26 @@
+import {WriteStreamsMock} from "../../../src/write-streams.js";
+import {handler} from "../../../src/handler.js";
+import {initSpawnSpy} from "../../mocks/utils.mock.js";
+import {WhenStatics} from "../../mocks/when-statics.js";
+
+beforeAll(() => {
+    initSpawnSpy([...WhenStatics.all, WhenStatics.mockGitRemoteHttp]);
+});
+
+test.concurrent("include:project with a wildcard file path includes every match", async () => {
+    const writeStreams = new WriteStreamsMock();
+
+    await handler({
+        cwd: "tests/test-cases/include-project-file-wildcard",
+        noColor: true,
+        list: true,
+        stateDir: ".gitlab-ci-local-include-project-file-wildcard",
+    }, writeStreams);
+
+    const jobNames = writeStreams.stdoutLines
+        .filter(l => /^(build|test)\s/.test(l))
+        .map(l => l.split(/\s+/)[0])
+        .sort();
+
+    expect(jobNames).toEqual(["build", "test"]);
+});