diff --git a/src/wp-includes/class-http.php b/src/wp-includes/class-http.php
index 9d5fca0eab..2fd4c54ea6 100644
--- a/src/wp-includes/class-http.php
+++ b/src/wp-includes/class-http.php
@@ -362,6 +362,9 @@ class WP_Http {
 			}
 		}
 
+		// Work around a bug in Requests when the path starts with // See https://github.com/rmccue/Requests/issues/231
+		$url = preg_replace( '!^(\w+://[^/]+)//(.*)$!i', '$1/$2', $url );
+
 		try {
 			$requests_response = Requests::request( $url, $headers, $data, $type, $options );
 
diff --git a/tests/phpunit/tests/http/base.php b/tests/phpunit/tests/http/base.php
index 671e2ae08c..e1e5b0747c 100644
--- a/tests/phpunit/tests/http/base.php
+++ b/tests/phpunit/tests/http/base.php
@@ -376,5 +376,18 @@ abstract class WP_HTTP_UnitTestCase extends WP_UnitTestCase {
 		$this->assertTrue( ! is_wp_error( $res ), print_r( $res, true ) );
 	}
 
+	/**
+	 * @ticket 37733
+	 */
+	function test_url_with_double_slashes_path() {
+		$url = $this->redirection_script . '?rt=' . 0;
+
+		$path = parse_url( $url, PHP_URL_PATH );
+		$url = str_replace( $path, '/' . $path, $url );
+
+		$res = wp_remote_request( $url );
+		$this->assertNotWPError( $res );
+	}
+
 
 }