diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index fcc180d4..67fcf5b6 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -131,6 +131,20 @@ jobs:
           command: update
           args: --package log --precise 0.4.16
 
+      - name: Downgrade regex
+        uses: actions-rs/cargo@v1
+        if: ${{ matrix.rust == '1.63.0' }}
+        with:
+          command: update
+          args: --package regex --precise 1.9.6
+
+      - name: Downgrade half
+        uses: actions-rs/cargo@v1
+        if: ${{ matrix.rust == '1.63.0' || matrix.rust == '1.69.0' }}
+        with:
+          command: update
+          args: --package half --precise 2.2.1
+
       - name: Run tests
         uses: actions-rs/cargo@v1
         with:
@@ -174,6 +188,20 @@ jobs:
           toolchain: ${{ matrix.rust }}
           override: true
 
+      - name: Downgrade regex
+        uses: actions-rs/cargo@v1
+        if: ${{ matrix.rust == '1.63.0' }}
+        with:
+          command: update
+          args: --package regex --precise 1.9.6
+
+      - name: Downgrade half
+        uses: actions-rs/cargo@v1
+        if: ${{ matrix.rust == '1.63.0' }}
+        with:
+          command: update
+          args: --package half --precise 2.2.1
+
       - name: Run tests
         uses: actions-rs/cargo@v1
         with:
diff --git a/Cargo.toml b/Cargo.toml
index adec26c5..648bbaab 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -34,6 +34,7 @@ nix = { version = "0.29", default-features = false, features = ["signal"], optio
 [dev-dependencies]
 futures = "0.3.5"
 rustix = { version = "0.38", default-features = false, features = ["net"] }
+criterion = { version = "0.4" }
 
 [features]
 block_on = ["pin-utils"]
@@ -48,3 +49,7 @@ rustdoc-args = ["--cfg", "docsrs"]
 [[test]]
 name = "signals"
 harness = false
+
+[[bench]]
+name = "timer"
+harness = false
\ No newline at end of file
diff --git a/benches/timer.rs b/benches/timer.rs
new file mode 100644
index 00000000..144d77de
--- /dev/null
+++ b/benches/timer.rs
@@ -0,0 +1,100 @@
+use std::time::Duration;
+
+use calloop::timer::TimeoutAction;
+use criterion::{criterion_group, criterion_main, Criterion};
+
+fn single(c: &mut Criterion) {
+    let mut event_loop = calloop::EventLoop::<()>::try_new().unwrap();
+    let loop_handle = event_loop.handle();
+
+    let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10));
+    let mut timeout_token = loop_handle
+        .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+        .unwrap();
+
+    c.bench_function("extend_single", |b| {
+        b.iter(|| {
+            loop_handle.remove(timeout_token);
+
+            let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10));
+            timeout_token = loop_handle
+                .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+                .unwrap();
+
+            event_loop.dispatch(Some(Duration::ZERO), &mut ()).unwrap();
+        });
+    });
+}
+
+fn mixed(c: &mut Criterion) {
+    let mut event_loop = calloop::EventLoop::<()>::try_new().unwrap();
+    let loop_handle = event_loop.handle();
+
+    let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10 - 1));
+    loop_handle
+        .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+        .unwrap();
+
+    let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10));
+    let mut timeout_token = loop_handle
+        .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+        .unwrap();
+
+    let timer = calloop::timer::Timer::from_duration(Duration::from_secs(90 * 10));
+    loop_handle
+        .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+        .unwrap();
+
+    c.bench_function("extend_mixed", |b| {
+        b.iter(|| {
+            loop_handle.remove(timeout_token);
+
+            let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10));
+            timeout_token = loop_handle
+                .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+                .unwrap();
+
+            event_loop.dispatch(Some(Duration::ZERO), &mut ()).unwrap();
+        });
+    });
+}
+
+fn mixed_multiple(c: &mut Criterion) {
+    let mut event_loop = calloop::EventLoop::<()>::try_new().unwrap();
+    let loop_handle = event_loop.handle();
+
+    for _ in 0..1000 {
+        let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10 - 1));
+        loop_handle
+            .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+            .unwrap();
+    }
+
+    let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10));
+    let mut timeout_token = loop_handle
+        .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+        .unwrap();
+
+    for _ in 0..1000 {
+        let timer = calloop::timer::Timer::from_duration(Duration::from_secs(90 * 10));
+        loop_handle
+            .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+            .unwrap();
+    }
+
+    c.bench_function("extend_mixed_many", |b| {
+        b.iter(|| {
+            loop_handle.remove(timeout_token);
+
+            let timer = calloop::timer::Timer::from_duration(Duration::from_secs(60 * 10));
+            timeout_token = loop_handle
+                .insert_source(timer, |_, _, _| TimeoutAction::Drop)
+                .unwrap();
+
+            event_loop.dispatch(Some(Duration::ZERO), &mut ()).unwrap();
+        });
+    });
+}
+
+criterion_group!(benches, single, mixed, mixed_multiple);
+criterion_main!(benches);
diff --git a/src/sources/timer.rs b/src/sources/timer.rs
index 7a4cba85..b6331c9d 100644
--- a/src/sources/timer.rs
+++ b/src/sources/timer.rs
@@ -229,8 +229,19 @@ impl TimerWheel {
     }
 
     pub(crate) fn cancel(&mut self, counter: u32) {
+        if self
+            .heap
+            .peek()
+            .map(|data| data.counter == counter)
+            .unwrap_or(false)
+        {
+            self.heap.pop();
+            return;
+        };
+
         self.heap
             .iter()
+            .rev()
             .find(|data| data.counter == counter)
             .map(|data| data.token.take());
     }
@@ -265,6 +276,7 @@ impl TimerWheel {
 // trait implementations for TimeoutData
 
 impl std::cmp::Ord for TimeoutData {
+    #[inline]
     fn cmp(&self, other: &Self) -> std::cmp::Ordering {
         // earlier values have priority
         self.deadline.cmp(&other.deadline).reverse()
@@ -272,6 +284,7 @@ impl std::cmp::Ord for TimeoutData {
 }
 
 impl std::cmp::PartialOrd for TimeoutData {
+    #[inline]
     fn partial_cmp(&self, other: &Self) -> Option<std::cmp::Ordering> {
         Some(self.cmp(other))
     }
@@ -281,6 +294,7 @@ impl std::cmp::PartialOrd for TimeoutData {
 // and the type is private, so ignore its coverage
 impl std::cmp::PartialEq for TimeoutData {
     #[cfg_attr(feature = "nightly_coverage", coverage(off))]
+    #[inline]
     fn eq(&self, other: &Self) -> bool {
         self.deadline == other.deadline
     }