diff --git a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
index 98fec3f7c928b..8aebae18c1ae9 100644
--- a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
+++ b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
@@ -2478,6 +2478,37 @@ mod tests {
             regex_not_match(col("c1"), lit("^foo$")),
             col("c1").not_eq(lit("foo")),
         );
+
+        // regular expressions that match exact captured literals
+        assert_change(
+            regex_match(col("c1"), lit("^(foo|bar)$")),
+            col("c1").eq(lit("foo")).or(col("c1").eq(lit("bar"))),
+        );
+        assert_change(
+            regex_not_match(col("c1"), lit("^(foo|bar)$")),
+            col("c1")
+                .not_eq(lit("foo"))
+                .and(col("c1").not_eq(lit("bar"))),
+        );
+        assert_change(
+            regex_match(col("c1"), lit("^(foo)$")),
+            col("c1").eq(lit("foo")),
+        );
+        assert_change(
+            regex_match(col("c1"), lit("^(foo|bar|baz)$")),
+            ((col("c1").eq(lit("foo"))).or(col("c1").eq(lit("bar"))))
+                .or(col("c1").eq(lit("baz"))),
+        );
+        assert_change(
+            regex_match(col("c1"), lit("^(foo|bar|baz|qux)$")),
+            col("c1")
+                .in_list(vec![lit("foo"), lit("bar"), lit("baz"), lit("qux")], false),
+        );
+
+        // regular expressions that mismatch captured literals
+        assert_no_change(regex_match(col("c1"), lit("(foo|bar)")));
+        assert_no_change(regex_match(col("c1"), lit("(foo|bar)*")));
+        assert_no_change(regex_match(col("c1"), lit("^(foo|bar)*")));
         assert_no_change(regex_match(col("c1"), lit("^foo|bar$")));
         assert_no_change(regex_match(col("c1"), lit("^(foo)(bar)$")));
         assert_no_change(regex_match(col("c1"), lit("^")));
diff --git a/datafusion/optimizer/src/simplify_expressions/regex.rs b/datafusion/optimizer/src/simplify_expressions/regex.rs
index ca298abcfa00d..108f1774b42c0 100644
--- a/datafusion/optimizer/src/simplify_expressions/regex.rs
+++ b/datafusion/optimizer/src/simplify_expressions/regex.rs
@@ -17,7 +17,7 @@
 
 use datafusion_common::{DataFusionError, Result, ScalarValue};
 use datafusion_expr::{lit, BinaryExpr, Expr, Like, Operator};
-use regex_syntax::hir::{Hir, HirKind, Literal, Look};
+use regex_syntax::hir::{Capture, Hir, HirKind, Literal, Look};
 
 /// Maximum number of regex alternations (`foo|bar|...`) that will be expanded into multiple `LIKE` expressions.
 const MAX_REGEX_ALTERNATIONS_EXPANSION: usize = 4;
@@ -33,7 +33,6 @@ pub fn simplify_regex_expr(
         match regex_syntax::Parser::new().parse(pattern) {
             Ok(hir) => {
                 let kind = hir.kind();
-
                 if let HirKind::Alternation(alts) = kind {
                     if alts.len() <= MAX_REGEX_ALTERNATIONS_EXPANSION {
                         if let Some(expr) = lower_alt(&mode, &left, alts) {
@@ -166,6 +165,33 @@ fn is_anchored_literal(v: &[Hir]) -> bool {
         .all(|h| matches!(h.kind(), HirKind::Literal(_)))
 }
 
+/// returns true if the elements in a `Concat` pattern are:
+/// - `[Look::Start, Capture(Alternation(Literals...)), Look::End]`
+fn is_anchored_capture(v: &[Hir]) -> bool {
+    if v.len() != 3
+        || !matches!(
+            (v.first().unwrap().kind(), v.last().unwrap().kind()),
+            (&HirKind::Look(Look::Start), &HirKind::Look(Look::End))
+        )
+    {
+        return false;
+    }
+
+    if let HirKind::Capture(cap, ..) = v[1].kind() {
+        let Capture { sub, .. } = cap;
+        if let HirKind::Alternation(alters) = sub.kind() {
+            let has_non_literal = alters
+                .iter()
+                .any(|v| !matches!(v.kind(), &HirKind::Literal(_)));
+            if has_non_literal {
+                return false;
+            }
+        }
+    }
+
+    true
+}
+
 /// extracts a string literal expression assuming that [`is_anchored_literal`]
 /// returned true.
 fn anchored_literal_to_expr(v: &[Hir]) -> Option<Expr> {
@@ -179,6 +205,40 @@ fn anchored_literal_to_expr(v: &[Hir]) -> Option<Expr> {
     }
 }
 
+fn anchored_alternation_to_exprs(v: &[Hir]) -> Option<Vec<Expr>> {
+    if 3 != v.len() {
+        return None;
+    }
+
+    if let HirKind::Capture(cap, ..) = v[1].kind() {
+        let Capture { sub, .. } = cap;
+        if let HirKind::Alternation(alters) = sub.kind() {
+            let mut literals = Vec::with_capacity(alters.len());
+            for hir in alters {
+                let mut is_safe = false;
+                if let HirKind::Literal(l) = hir.kind() {
+                    if let Some(safe_literal) = str_from_literal(l).map(lit) {
+                        literals.push(safe_literal);
+                        is_safe = true;
+                    }
+                }
+
+                if !is_safe {
+                    return None;
+                }
+            }
+
+            return Some(literals);
+        } else if let HirKind::Literal(l) = sub.kind() {
+            if let Some(safe_literal) = str_from_literal(l).map(lit) {
+                return Some(vec![safe_literal]);
+            }
+            return None;
+        }
+    }
+    None
+}
+
 fn lower_simple(mode: &OperatorMode, left: &Expr, hir: &Hir) -> Option<Expr> {
     match hir.kind() {
         HirKind::Empty => {
@@ -189,10 +249,13 @@ fn lower_simple(mode: &OperatorMode, left: &Expr, hir: &Hir) -> Option<Expr> {
             return Some(mode.expr(Box::new(left.clone()), format!("%{s}%")));
         }
         HirKind::Concat(inner) if is_anchored_literal(inner) => {
-            let right = anchored_literal_to_expr(inner)?;
-            return Some(
-                mode.expr_matches_literal(Box::new(left.clone()), Box::new(right)),
-            );
+            return anchored_literal_to_expr(inner).map(|right| {
+                mode.expr_matches_literal(Box::new(left.clone()), Box::new(right))
+            });
+        }
+        HirKind::Concat(inner) if is_anchored_capture(inner) => {
+            return anchored_alternation_to_exprs(inner)
+                .map(|right| left.clone().in_list(right, mode.not));
         }
         HirKind::Concat(inner) => {
             if let Some(pattern) = collect_concat_to_like_string(inner) {
@@ -201,7 +264,6 @@ fn lower_simple(mode: &OperatorMode, left: &Expr, hir: &Hir) -> Option<Expr> {
         }
         _ => {}
     }
-
     None
 }