diff --git a/Cargo.lock b/Cargo.lock
index 0851dc587..8f87fc1ad 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -30,9 +30,9 @@ dependencies = [
 
 [[package]]
 name = "aho-corasick"
-version = "0.7.20"
+version = "1.0.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "cc936419f96fa211c1b9166887b38e5e40b19958e5b895be7c1f93adec7071ac"
+checksum = "86b8f9420f797f2d9e935edf629310eb938a0d839f984e25327f3c7eed22300c"
 dependencies = [
  "memchr",
 ]
@@ -474,6 +474,7 @@ dependencies = [
  "hyper",
  "lazy_static",
  "rand 0.8.5",
+ "regex",
  "reqwest",
  "rocket",
  "schemars 0.8.12",
@@ -2220,7 +2221,7 @@ version = "0.1.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8263075bb86c5a1b1427b5ae862e8889656f126e9f77c484496e8b47cf5c5558"
 dependencies = [
- "regex-automata",
+ "regex-automata 0.1.10",
 ]
 
 [[package]]
@@ -2985,13 +2986,14 @@ dependencies = [
 
 [[package]]
 name = "regex"
-version = "1.7.1"
+version = "1.9.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "48aaa5748ba571fb95cd2c85c09f629215d3a6ece942baa100950af03a34f733"
+checksum = "81bc1d4caf89fac26a70747fe603c130093b53c773888797a6329091246d651a"
 dependencies = [
  "aho-corasick",
  "memchr",
- "regex-syntax",
+ "regex-automata 0.3.6",
+ "regex-syntax 0.7.4",
 ]
 
 [[package]]
@@ -3000,7 +3002,18 @@ version = "0.1.10"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6c230d73fb8d8c1b9c0b3135c5142a8acee3a0558fb8db5cf1cb65f8d7862132"
 dependencies = [
- "regex-syntax",
+ "regex-syntax 0.6.28",
+]
+
+[[package]]
+name = "regex-automata"
+version = "0.3.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fed1ceff11a1dddaee50c9dc8e4938bd106e9d89ae372f192311e7da498e3b69"
+dependencies = [
+ "aho-corasick",
+ "memchr",
+ "regex-syntax 0.7.4",
 ]
 
 [[package]]
@@ -3009,6 +3022,12 @@ version = "0.6.28"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "456c603be3e8d448b072f410900c09faf164fbce2d480456f50eea6e25f9c848"
 
+[[package]]
+name = "regex-syntax"
+version = "0.7.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e5ea92a5b6195c6ef2a0295ea818b312502c6fc94dde986c5553242e18fd4ce2"
+
 [[package]]
 name = "remove_dir_all"
 version = "0.5.3"
diff --git a/components/chainhook-cli/src/cli/mod.rs b/components/chainhook-cli/src/cli/mod.rs
index c03199fcf..28eb37783 100644
--- a/components/chainhook-cli/src/cli/mod.rs
+++ b/components/chainhook-cli/src/cli/mod.rs
@@ -339,7 +339,7 @@ async fn handle_command(opts: Opts, ctx: Context) -> Result<(), String> {
                             start_block: Some(34239),
                             end_block: Some(50000),
                             blocks: None,
-                            predicate: StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+                            predicate: StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
                                 contract_identifier: "ST1SVA0SST0EDT4MFYGWGP6GNSXMMQJDVP1G8QTTC.arkadiko-freddie-v1-1".into(),
                                 contains: "vault".into(),
                             }),
@@ -355,7 +355,7 @@ async fn handle_command(opts: Opts, ctx: Context) -> Result<(), String> {
                             start_block: Some(34239),
                             end_block: Some(50000),
                             blocks: None,
-                            predicate: StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+                            predicate: StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
                                 contract_identifier: "SP2C2YFP12AJZB4MABJBAJ55XECVS7E4PMMZ89YZR.arkadiko-freddie-v1-1".into(),
                                 contains: "vault".into(),
                             }),
diff --git a/components/chainhook-cli/src/service/tests/mod.rs b/components/chainhook-cli/src/service/tests/mod.rs
index 8fbe52f46..a8d9cfcb4 100644
--- a/components/chainhook-cli/src/service/tests/mod.rs
+++ b/components/chainhook-cli/src/service/tests/mod.rs
@@ -308,6 +308,7 @@ async fn it_handles_stacks_predicates_with_network(network: &str) {
 #[test_case(json!({"scope":"print_event","contract_identifier": "ST1PQHQKV0RJXZFY1DGX8MNSNYVE3VGZJSRTPGZGM.monkey-sip09", "contains": "*"}); "with scope print_event wildcard conatins")]
 #[test_case(json!({"scope":"print_event","contract_identifier": "*", "contains": "vault"}); "with scope print_event wildcard contract_identifier")]
 #[test_case(json!({"scope":"print_event", "contract_identifier": "*", "contains": "*"}); "with scope print_event wildcard both fields")]
+#[test_case(json!({"scope":"print_event", "contract_identifier": "*", "matches_regex": "(some)|(value)"}); "with scope print_event and matching_rule regex")]
 #[test_case(json!({"scope":"ft_event","asset_identifier": "ST1PQHQKV0RJXZFY1DGX8MNSNYVE3VGZJSRTPGZGM.cbtc-token::cbtc","actions": ["burn"]}); "with scope ft_event")]
 #[test_case(json!({"scope":"nft_event","asset_identifier": "ST1PQHQKV0RJXZFY1DGX8MNSNYVE3VGZJSRTPGZGM.monkey-sip09::monkeys","actions": ["mint", "transfer", "burn"]}); "with scope nft_event")]
 #[test_case(json!({"scope":"stx_event","actions": ["transfer", "lock"]}); "with scope stx_event")]
diff --git a/components/chainhook-sdk/Cargo.toml b/components/chainhook-sdk/Cargo.toml
index 58c7d201d..923946362 100644
--- a/components/chainhook-sdk/Cargo.toml
+++ b/components/chainhook-sdk/Cargo.toml
@@ -41,6 +41,7 @@ zeromq = { version = "0.3.3", default-features = false, features = ["tokio-runti
 dashmap = "5.4.0"
 fxhash = "0.2.1"
 lazy_static = "1.4.0"
+regex = "1.9.3"
 
 [dev-dependencies]
 test-case = "3.1.0"
diff --git a/components/chainhook-sdk/src/chainhooks/stacks/mod.rs b/components/chainhook-sdk/src/chainhooks/stacks/mod.rs
index 680be7e34..2cb5c4585 100644
--- a/components/chainhook-sdk/src/chainhooks/stacks/mod.rs
+++ b/components/chainhook-sdk/src/chainhooks/stacks/mod.rs
@@ -2,13 +2,14 @@ use crate::utils::{AbstractStacksBlock, Context};
 
 use super::types::{
     BlockIdentifierIndexRule, ExactMatchingRule, HookAction, StacksChainhookSpecification,
-    StacksContractDeploymentPredicate, StacksPredicate,
+    StacksContractDeploymentPredicate, StacksPredicate, StacksPrintEventBasedPredicate,
 };
 use chainhook_types::{
     BlockIdentifier, StacksChainEvent, StacksTransactionData, StacksTransactionEvent,
     StacksTransactionKind, TransactionIdentifier,
 };
 use hiro_system_kit::slog;
+use regex::Regex;
 use reqwest::{Client, Method};
 use serde_json::Value as JsonValue;
 use stacks_rpc_client::clarity::stacks_common::codec::StacksMessageCodec;
@@ -406,16 +407,47 @@ pub fn evaluate_stacks_predicate_on_transaction<'a>(
                 match event {
                     StacksTransactionEvent::SmartContractEvent(actual) => {
                         if actual.topic == "print" {
-                            if expected_event.contract_identifier == actual.contract_identifier
-                                || expected_event.contract_identifier == "*"
-                            {
-                                if expected_event.contains == "*" {
-                                    return true;
+                            match expected_event {
+                                StacksPrintEventBasedPredicate::Contains {
+                                    contract_identifier,
+                                    contains,
+                                } => {
+                                    if contract_identifier == &actual.contract_identifier
+                                        || contract_identifier == "*"
+                                    {
+                                        if contains == "*" {
+                                            return true;
+                                        }
+                                        let value = format!(
+                                            "{}",
+                                            expect_decoded_clarity_value(&actual.hex_value)
+                                        );
+                                        if value.contains(contains) {
+                                            return true;
+                                        }
+                                    }
                                 }
-                                let value =
-                                    format!("{}", expect_decoded_clarity_value(&actual.hex_value));
-                                if value.contains(&expected_event.contains) {
-                                    return true;
+                                StacksPrintEventBasedPredicate::MatchesRegex {
+                                    contract_identifier,
+                                    regex,
+                                } => {
+                                    if contract_identifier == &actual.contract_identifier
+                                        || contract_identifier == "*"
+                                    {
+                                        if let Ok(regex) = Regex::new(regex) {
+                                            let value = format!(
+                                                "{}",
+                                                expect_decoded_clarity_value(&actual.hex_value)
+                                            );
+                                            if regex.is_match(&value) {
+                                                return true;
+                                            }
+                                        } else {
+                                            ctx.try_log(|logger| {
+                                                slog::error!(logger, "unable to parse print_event matching rule as regex")
+                                            });
+                                        }
+                                    }
                                 }
                             }
                         }
diff --git a/components/chainhook-sdk/src/chainhooks/tests/mod.rs b/components/chainhook-sdk/src/chainhooks/tests/mod.rs
index 82e2cb2b7..a3a458d93 100644
--- a/components/chainhook-sdk/src/chainhooks/tests/mod.rs
+++ b/components/chainhook-sdk/src/chainhooks/tests/mod.rs
@@ -227,7 +227,7 @@ pub mod fixtures;
 // PrintEvent predicate tests
 #[test_case(
     vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
-    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
         contract_identifier: "ST3AXH4EBHD63FCFPTZ8GR29TNTVWDYPGY0KDY5E5.loan-data".to_string(),
         contains: "some-value".to_string()
     }),
@@ -236,7 +236,7 @@ pub mod fixtures;
 )]
 #[test_case(
     vec![vec![get_test_event_by_type("smart_contract_not_print_event")]], 
-    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
         contract_identifier: "ST3AXH4EBHD63FCFPTZ8GR29TNTVWDYPGY0KDY5E5.loan-data".to_string(),
         contains: "some-value".to_string(),
     }),
@@ -245,7 +245,7 @@ pub mod fixtures;
 )]
 #[test_case(
     vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
-    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
         contract_identifier: "wront-id".to_string(),
         contains: "some-value".to_string(),
     }),
@@ -254,7 +254,7 @@ pub mod fixtures;
 )]
 #[test_case(
     vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
-    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
         contract_identifier:
             "ST3AXH4EBHD63FCFPTZ8GR29TNTVWDYPGY0KDY5E5.loan-data".to_string(),
         contains: "wrong-value".to_string(),
@@ -264,7 +264,7 @@ pub mod fixtures;
 )]
 #[test_case(
     vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
-    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
         contract_identifier: "*".to_string(),
         contains: "some-value".to_string(),
     }),
@@ -273,7 +273,7 @@ pub mod fixtures;
 )]
 #[test_case(
     vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
-    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
         contract_identifier: "ST3AXH4EBHD63FCFPTZ8GR29TNTVWDYPGY0KDY5E5.loan-data".to_string(),
         contains: "*".to_string(),
     }),
@@ -282,13 +282,41 @@ pub mod fixtures;
 )]
 #[test_case(
     vec![vec![get_test_event_by_type("smart_contract_print_event")], vec![get_test_event_by_type("smart_contract_print_event_empty")]], 
-    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate {
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::Contains {
         contract_identifier: "*".to_string(),
         contains: "*".to_string(),
     }),
     2;
     "PrintEvent predicate contract_identifier wildcard and contains wildcard matches all values on all print events"
 )]
+#[test_case(
+    vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::MatchesRegex {
+        contract_identifier: "ST3AXH4EBHD63FCFPTZ8GR29TNTVWDYPGY0KDY5E5.loan-data".to_string(),
+        regex: "(some)|(value)".to_string(),
+    }),
+    1;
+    "PrintEvent predicate matches contract_identifier and regex"
+)]
+#[test_case(
+    vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::MatchesRegex {
+        contract_identifier: "*".to_string(),
+        regex: "(some)|(value)".to_string(),
+    }),
+    1;
+    "PrintEvent predicate contract_identifier wildcard checks all print events for match with regex"
+)]
+#[test_case(
+    vec![vec![get_test_event_by_type("smart_contract_print_event")]], 
+    StacksPredicate::PrintEvent(StacksPrintEventBasedPredicate::MatchesRegex {
+        contract_identifier: "*".to_string(),
+        regex: "[".to_string(),
+    }),
+    0
+    ;
+    "PrintEvent predicate does not match invalid regex"
+)]
 fn test_stacks_predicates(
     blocks_with_events: Vec<Vec<StacksTransactionEvent>>,
     predicate: StacksPredicate,
diff --git a/components/chainhook-sdk/src/chainhooks/types.rs b/components/chainhook-sdk/src/chainhooks/types.rs
index 0a1c179a5..12e903fb3 100644
--- a/components/chainhook-sdk/src/chainhooks/types.rs
+++ b/components/chainhook-sdk/src/chainhooks/types.rs
@@ -776,9 +776,17 @@ pub enum StacksTrait {
 
 #[derive(Clone, Debug, Serialize, Deserialize, PartialEq, JsonSchema)]
 #[serde(rename_all = "snake_case")]
-pub struct StacksPrintEventBasedPredicate {
-    pub contract_identifier: String,
-    pub contains: String,
+#[serde(untagged)]
+pub enum StacksPrintEventBasedPredicate {
+    Contains {
+        contract_identifier: String,
+        contains: String,
+    },
+    MatchesRegex {
+        contract_identifier: String,
+        #[serde(rename = "matches_regex")]
+        regex: String,
+    },
 }
 
 #[derive(Clone, Debug, Serialize, Deserialize, PartialEq, JsonSchema)]
diff --git a/docs/chainhook-openapi.json b/docs/chainhook-openapi.json
index d09ef8f19..8f0c72e9d 100644
--- a/docs/chainhook-openapi.json
+++ b/docs/chainhook-openapi.json
@@ -2,7 +2,7 @@
   "openapi": "3.0.0",
   "info": {
     "title": "chainhook",
-    "version": "0.17.0"
+    "version": "1.0.0"
   },
   "paths": {
     "/ping": {
@@ -997,9 +997,39 @@
           },
           {
             "type": "object",
+            "anyOf": [
+              {
+                "type": "object",
+                "required": [
+                  "contains",
+                  "contract_identifier"
+                ],
+                "properties": {
+                  "contract_identifier": {
+                    "type": "string"
+                  },
+                  "contains": {
+                    "type": "string"
+                  }
+                }
+              },
+              {
+                "type": "object",
+                "required": [
+                  "contract_identifier",
+                  "matches_regex"
+                ],
+                "properties": {
+                  "contract_identifier": {
+                    "type": "string"
+                  },
+                  "matches_regex": {
+                    "type": "string"
+                  }
+                }
+              }
+            ],
             "required": [
-              "contains",
-              "contract_identifier",
               "scope"
             ],
             "properties": {
@@ -1008,12 +1038,6 @@
                 "enum": [
                   "print_event"
                 ]
-              },
-              "contract_identifier": {
-                "type": "string"
-              },
-              "contains": {
-                "type": "string"
               }
             }
           },