diff --git a/vortex-bench/src/clickbench/benchmark.rs b/vortex-bench/src/clickbench/benchmark.rs
index 2885dc29c3b..c036d1c084b 100644
--- a/vortex-bench/src/clickbench/benchmark.rs
+++ b/vortex-bench/src/clickbench/benchmark.rs
@@ -41,7 +41,7 @@ impl ClickBenchBenchmark {
     }
 }
 
-/// ClickBench sorted by event date and event time.
+/// ClickBench sorted by event time, with shard filenames shuffled to exercise sort pushdown.
 pub struct ClickBenchSortedBenchmark {
     pub queries_file: Option<String>,
     pub data_url: Url,
diff --git a/vortex-bench/src/clickbench/data.rs b/vortex-bench/src/clickbench/data.rs
index 7347e9fa1ba..bd570d6536c 100644
--- a/vortex-bench/src/clickbench/data.rs
+++ b/vortex-bench/src/clickbench/data.rs
@@ -34,11 +34,14 @@ use crate::datasets::data_downloads::download_data;
 use crate::datasets::data_downloads::download_many;
 use crate::utils::file::temp_download_filepath;
 
-/// Benchmark and local data directory name for ClickBench sorted by event date/time.
+/// Benchmark and local data directory name for ClickBench sorted by event time.
 pub const CLICKBENCH_SORTED_NAME: &str = "clickbench-sorted";
 const CLICKBENCH_PARTITIONED_NAME: &str = "clickbench_partitioned";
 const SORTED_SHARD_COUNT: usize = 100;
 const SORTED_SHARD_COUNT_U64: u64 = 100;
+const SORTED_SHARD_FILENAME_WIDTH: usize = 3;
+const SORTED_SHARD_PERMUTATION_MULTIPLIER: u64 = 37;
+const SORTED_SHARD_PERMUTATION_OFFSET: u64 = 17;
 
 /// Zero-based ClickBench query IDs that filter by or order/group on `EventDate`/`EventTime`.
 pub const CLICKBENCH_SORTED_QUERY_IDS: &[usize] = &[23, 24, 26, 36, 37, 38, 39, 40, 41, 42];
@@ -235,13 +238,18 @@ impl Flavor {
     }
 }
 
-/// Generate globally sorted ClickBench Parquet shards under `basepath`.
+/// Generate sorted ClickBench Parquet shards under `basepath`.
+///
+/// Each shard contains a contiguous `EventTime` range, but the shard filenames are deterministically
+/// shuffled. That makes ordinary file listing order bad for ascending TopK queries, so file sort
+/// pushdown has a visible job to do.
 pub async fn generate_sorted_clickbench(basepath: impl AsRef<Path>) -> anyhow::Result<()> {
+    let basepath = basepath.as_ref();
     let source_base = CLICKBENCH_PARTITIONED_NAME.to_data_path();
     Flavor::Partitioned.download(&source_base).await?;
 
     let source_parquet_dir = source_base.join(Format::Parquet.name());
-    let output_parquet_dir = basepath.as_ref().join(Format::Parquet.name());
+    let output_parquet_dir = basepath.join(Format::Parquet.name());
 
     if output_parquet_dir.exists() {
         info!(
@@ -374,7 +382,7 @@ PRAGMA temp_directory={temp_dir};
 CREATE TABLE hits_sorted AS
     SELECT *
     FROM read_parquet({source_glob})
-    ORDER BY \"EventDate\", \"EventTime\", \"WatchID\";
+    ORDER BY \"EventTime\";
 ",
         temp_dir = sql_string_literal(&duckdb_temp_dir.display().to_string()),
         source_glob = sql_string_literal(&source_glob.display().to_string()),
@@ -383,7 +391,7 @@ CREATE TABLE hits_sorted AS
     for shard_idx in 0..SORTED_SHARD_COUNT_U64 {
         let start = shard_idx * rows_per_shard;
         let end = (start + rows_per_shard).min(source_rows);
-        let output_path = output_parquet_dir.join(format!("hits_{shard_idx}.parquet"));
+        let output_path = output_parquet_dir.join(sorted_shard_file_name(shard_idx));
         script.push_str(&format!(
             "\
 COPY (
@@ -400,6 +408,21 @@ COPY (
     script
 }
 
+fn sorted_shard_file_name(sorted_shard_idx: u64) -> String {
+    debug_assert!(sorted_shard_idx < SORTED_SHARD_COUNT_U64);
+    let listing_shard_idx = sorted_shard_listing_idx(sorted_shard_idx);
+    format!(
+        "hits_{listing_shard_idx:0width$}.parquet",
+        width = SORTED_SHARD_FILENAME_WIDTH
+    )
+}
+
+fn sorted_shard_listing_idx(sorted_shard_idx: u64) -> u64 {
+    debug_assert!(sorted_shard_idx < SORTED_SHARD_COUNT_U64);
+    (sorted_shard_idx * SORTED_SHARD_PERMUTATION_MULTIPLIER + SORTED_SHARD_PERMUTATION_OFFSET)
+        % SORTED_SHARD_COUNT_U64
+}
+
 fn parquet_dir_row_count(parquet_dir: &Path) -> anyhow::Result<u64> {
     let files = parquet_files(parquet_dir)?;
     anyhow::ensure!(
@@ -450,3 +473,58 @@ fn sql_string_literal(value: &str) -> String {
 fn quote_identifier(value: &str) -> String {
     format!("\"{}\"", value.replace('"', "\"\""))
 }
+
+#[cfg(test)]
+mod tests {
+    use vortex::utils::aliases::hash_set::HashSet;
+
+    use super::*;
+
+    #[test]
+    fn sorted_clickbench_shard_names_use_deterministic_shuffle() {
+        let names = (0..SORTED_SHARD_COUNT_U64)
+            .map(sorted_shard_file_name)
+            .collect::<Vec<_>>();
+
+        assert_eq!(names[0], "hits_017.parquet");
+        assert_eq!(names[1], "hits_054.parquet");
+        assert_eq!(names[2], "hits_091.parquet");
+        assert_eq!(names[99], "hits_080.parquet");
+
+        let unique_names = names.iter().collect::<HashSet<_>>();
+        assert_eq!(unique_names.len(), SORTED_SHARD_COUNT);
+
+        let mut sorted_names = names.clone();
+        sorted_names.sort();
+        assert_ne!(names, sorted_names);
+
+        let mut reverse_names = sorted_names;
+        reverse_names.reverse();
+        assert_ne!(names, reverse_names);
+    }
+
+    #[test]
+    fn sorted_clickbench_script_sorts_for_topk_and_writes_shuffled_shards() {
+        let script = sorted_clickbench_duckdb_script(
+            Path::new("source"),
+            Path::new("out"),
+            Path::new("tmp"),
+            1000,
+        );
+
+        assert!(script.contains("ORDER BY \"EventTime\";"));
+
+        let first = script
+            .find("hits_017.parquet")
+            .expect("first sorted shard should use its shuffled shard name");
+        let second = script
+            .find("hits_054.parquet")
+            .expect("second sorted shard should use its shuffled shard name");
+        let third = script
+            .find("hits_091.parquet")
+            .expect("third sorted shard should use its shuffled shard name");
+
+        assert!(first < second);
+        assert!(second < third);
+    }
+}