diff --git a/Cargo.lock b/Cargo.lock
index 57be369d7c3..00f5345aa76 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -10227,6 +10227,7 @@ dependencies = [
  "datafusion-sqllogictest",
  "futures",
  "indicatif",
+ "regex",
  "rstest",
  "sqllogictest",
  "thiserror 2.0.18",
diff --git a/vortex-sqllogictest/Cargo.toml b/vortex-sqllogictest/Cargo.toml
index 757abb49689..499702454f3 100644
--- a/vortex-sqllogictest/Cargo.toml
+++ b/vortex-sqllogictest/Cargo.toml
@@ -22,6 +22,7 @@ datafusion = { workspace = true }
 datafusion-sqllogictest = { workspace = true }
 futures.workspace = true
 indicatif.workspace = true
+regex = { workspace = true }
 rstest = { workspace = true }
 sqllogictest = "0.29.1"
 thiserror = { workspace = true }
diff --git a/vortex-sqllogictest/src/duckdb.rs b/vortex-sqllogictest/src/duckdb.rs
index 182110e1f45..821eaeeed6b 100644
--- a/vortex-sqllogictest/src/duckdb.rs
+++ b/vortex-sqllogictest/src/duckdb.rs
@@ -10,11 +10,13 @@ use async_trait::async_trait;
 use bigdecimal::BigDecimal;
 use datafusion_sqllogictest::DFColumnType;
 use indicatif::ProgressBar;
+use regex::RegexBuilder;
 use sqllogictest::DBOutput;
 use sqllogictest::Normalizer;
 use sqllogictest::runner::AsyncDB;
 use vortex::error::VortexError;
 use vortex::error::VortexExpect;
+use vortex::error::vortex_err;
 use vortex_duckdb::duckdb::Connection;
 use vortex_duckdb::duckdb::Database;
 use vortex_duckdb::duckdb::ExtractedValue;
@@ -99,20 +101,48 @@ impl DuckDB {
     }
 }
 
+// Regex matching for output inspired by Duckdb's .test files. Rows joined
+// by newline are matched against positive or negative match.
+const REGEX_MARKER: &str = "<REGEX>:";
+const NEG_REGEX_MARKER: &str = "<!REGEX>:";
+
+fn regex_matches(pattern: &str, text: &str) -> bool {
+    RegexBuilder::new(pattern)
+        .dot_matches_new_line(true)
+        .build()
+        .map_err(|e| vortex_err!("invalid regex pattern: {e}"))
+        .vortex_expect("invalid <REGEX> pattern")
+        .is_match(text)
+}
+
 pub fn duckdb_validator(
     normalizer: Normalizer,
     actual: &[Vec<String>],
     expected: &[String],
 ) -> bool {
-    let actual = actual.iter().flat_map(|strings| {
-        strings
-            .join(" ")
-            .trim_end()
-            .split('\n')
-            .map(|line| line.trim_end().to_string())
-            .collect::<Vec<_>>()
-    });
-    Iterator::eq(actual, expected.iter().map(normalizer))
+    let actual = actual
+        .iter()
+        .flat_map(|strings| {
+            strings
+                .join(" ")
+                .trim_end()
+                .split('\n')
+                .map(|line| line.trim_end().to_string())
+                .collect::<Vec<_>>()
+        })
+        .collect::<Vec<_>>();
+    let expected = expected.iter().map(normalizer).collect::<Vec<_>>();
+
+    if let [line] = expected.as_slice() {
+        if let Some(pattern) = line.strip_prefix(NEG_REGEX_MARKER) {
+            return !regex_matches(pattern, &actual.join("\n"));
+        }
+        if let Some(pattern) = line.strip_prefix(REGEX_MARKER) {
+            return regex_matches(pattern, &actual.join("\n"));
+        }
+    }
+
+    Iterator::eq(actual.iter(), expected.iter())
 }
 
 #[async_trait]
@@ -274,11 +304,78 @@ mod tests {
     use vortex_duckdb::duckdb::Value;
 
     use super::ValueDisplayAdapter;
+    use super::duckdb_validator;
+    use super::regex_matches;
 
     fn display(value: Value) -> String {
         ValueDisplayAdapter(value).to_string()
     }
 
+    #[rstest]
+    #[case("foo", "foo", true)]
+    #[case("foo", "xfooy", true)]
+    #[case("foo", "bar", false)]
+    #[case("^foo$", "foo", true)]
+    #[case("^foo$", "xfoo", false)]
+    #[case("a.*b", "axxxb", true)]
+    #[case("a.*b", "a\nxx\nb", true)]
+    #[case("needle", "line1\nneedle here\nline3", true)]
+    #[case("missing", "line1\nline2\nline3", false)]
+    fn test_regex_matches(#[case] pattern: &str, #[case] text: &str, #[case] expected: bool) {
+        assert_eq!(regex_matches(pattern, text), expected);
+    }
+
+    // clippy: Signature must match sqllogictest::Normalizer
+    #[expect(clippy::ptr_arg)]
+    fn identity(s: &String) -> String {
+        s.clone()
+    }
+
+    #[test]
+    fn validator_regex_directive_spans_multiple_lines() {
+        let actual = vec![vec![
+            "physical_plan".to_string(),
+            "[\n  {\n    \"SELECT projections\": \"str\"\n  }\n]".to_string(),
+        ]];
+
+        assert!(duckdb_validator(
+            identity,
+            &actual,
+            &["<REGEX>:SELECT projections".to_string()]
+        ));
+        assert!(!duckdb_validator(
+            identity,
+            &actual,
+            &["<REGEX>:NOT PRESENT".to_string()]
+        ));
+
+        assert!(duckdb_validator(
+            identity,
+            &actual,
+            &["<!REGEX>:NOT PRESENT".to_string()]
+        ));
+        assert!(!duckdb_validator(
+            identity,
+            &actual,
+            &["<!REGEX>:SELECT projections".to_string()]
+        ));
+    }
+
+    #[test]
+    fn validator_without_marker_requires_exact_match() {
+        let actual = vec![vec!["5".to_string()], vec!["3".to_string()]];
+        assert!(duckdb_validator(
+            identity,
+            &actual,
+            &["5".to_string(), "3".to_string()]
+        ));
+        assert!(!duckdb_validator(
+            identity,
+            &actual,
+            &["5".to_string(), "2".to_string()]
+        ));
+    }
+
     #[test]
     fn test_null() {
         assert_eq!(display(Value::sql_null()), "NULL");