diff --git a/tools/install/bazel/test/drake_bazel_installed_test.py b/tools/install/bazel/test/drake_bazel_installed_test.py
index eed046eb945b..18b2a042abc6 100644
--- a/tools/install/bazel/test/drake_bazel_installed_test.py
+++ b/tools/install/bazel/test/drake_bazel_installed_test.py
@@ -27,12 +27,12 @@ def main():
 
     # The commit (version) here should be identical to the commit listed in
     # drake/tools/workspace/rules_python/repository.bzl.
-    rules_python_commit = "0.24.0"
+    rules_python_commit = "0.25.0"
     rules_python_urls = [
         f"https://github.com/bazelbuild/rules_python/archive/{rules_python_commit}.tar.gz",  # noqa
         f"https://drake-mirror.csail.mit.edu/github/bazelbuild/rules_python/{rules_python_commit}.tar.gz",  # noqa
     ]
-    rules_python_sha256 = "0a8003b044294d7840ac7d9d73eef05d6ceb682d7516781a4ec62eeb34702578"  # noqa
+    rules_python_sha256 = "5868e73107a8e85d8f323806e60cad7283f34b32163ea6ff1020cf27abef6036"  # noqa
 
     with open(join(scratch_dir, "WORKSPACE"), "w") as f:
         f.write(f"""
diff --git a/tools/workspace/buildifier/repository.bzl b/tools/workspace/buildifier/repository.bzl
index 6ff5841d4984..6b1604131b25 100644
--- a/tools/workspace/buildifier/repository.bzl
+++ b/tools/workspace/buildifier/repository.bzl
@@ -33,17 +33,17 @@ def _impl(repository_ctx):
     # To update this, each artifact needs to be downloaded and its checksum
     # computed manually.  See tools/workspace/mirrors.bzl for the canonical
     # URL.
-    version = "v6.1.2"
+    version = "v6.3.3"
     darwin_urls = [
         x.format(version = version, filename = "buildifier-darwin-amd64")
         for x in repository_ctx.attr.mirrors.get("buildifier")
     ]
-    darwin_sha256 = "e2f4a67691c5f55634fbfb3850eb97dd91be0edd059d947b6c83d120682e0216"  # noqa
+    darwin_sha256 = "3c36a3217bd793815a907a8e5bf81c291e2d35d73c6073914640a5f42e65f73f"  # noqa
     linux_urls = [
         x.format(version = version, filename = "buildifier-linux-amd64")
         for x in repository_ctx.attr.mirrors.get("buildifier")
     ]
-    linux_sha256 = "51bc947dabb7b14ec6fb1224464fbcf7a7cb138f1a10a3b328f00835f72852ce"  # noqa
+    linux_sha256 = "42f798ec532c58e34401985043e660cb19d5ae994e108d19298c7d229547ffca"  # noqa
 
     # Choose which binary to use.
     os_result = determine_os(repository_ctx)
diff --git a/tools/workspace/googlebenchmark/repository.bzl b/tools/workspace/googlebenchmark/repository.bzl
index a22c575998c0..6785304d8e15 100644
--- a/tools/workspace/googlebenchmark/repository.bzl
+++ b/tools/workspace/googlebenchmark/repository.bzl
@@ -6,8 +6,8 @@ def googlebenchmark_repository(
     github_archive(
         name = name,
         repository = "google/benchmark",
-        commit = "v1.8.2",
-        sha256 = "2aab2980d0376137f969d92848fbb68216abb07633034534fc8c65cc4e7a0e93",  # noqa
+        commit = "v1.8.3",
+        sha256 = "6bc180a57d23d4d9515519f92b0c83d61b05b5bab188961f36ac7b06b0d9e9ce",  # noqa
         mirrors = mirrors,
         patches = [
             ":patches/console_allocs.patch",
diff --git a/tools/workspace/gymnasium_py/repository.bzl b/tools/workspace/gymnasium_py/repository.bzl
index 560afbabd9cb..0df0425b3433 100644
--- a/tools/workspace/gymnasium_py/repository.bzl
+++ b/tools/workspace/gymnasium_py/repository.bzl
@@ -6,8 +6,8 @@ def gymnasium_py_repository(
     github_archive(
         name = name,
         repository = "Farama-Foundation/Gymnasium",
-        commit = "v0.29.0",
-        sha256 = "3a108018cf50dc327bfc66e479c280b8112de597804ceeaa3cc50860a2905115",  # noqa
+        commit = "v0.29.1",
+        sha256 = "0bff5ff33335ffe170f9ccba544f7c4d78e7b4dd883337f2ee00f8ba3c6d85b5",  # noqa
         build_file = ":package.BUILD.bazel",
         mirrors = mirrors,
     )
diff --git a/tools/workspace/mypy_internal/repository.bzl b/tools/workspace/mypy_internal/repository.bzl
index 147b97aeb640..39620407e4f9 100644
--- a/tools/workspace/mypy_internal/repository.bzl
+++ b/tools/workspace/mypy_internal/repository.bzl
@@ -9,8 +9,8 @@ def mypy_internal_repository(
         # drake/tools/workspace/new_release.py.  When practical, all members
         # of this cohort should be updated at the same time.
         repository = "python/mypy",
-        commit = "v1.4.1",
-        sha256 = "e3216a2e9f612d3b4e5f5b6f9404c571ae2c0f27a83e648b8758c73e902537dc",  # noqa
+        commit = "v1.5.1",
+        sha256 = "22894445313d989109498ea7a6b124034ab10cbb2b50f3878b81883eaa3290d2",  # noqa
         build_file = ":package.BUILD.bazel",
         patches = [
             ":patches/reject_double_colon.patch",
diff --git a/tools/workspace/rules_python/repository.bzl b/tools/workspace/rules_python/repository.bzl
index a38a0ea31d84..f2f3589c751d 100644
--- a/tools/workspace/rules_python/repository.bzl
+++ b/tools/workspace/rules_python/repository.bzl
@@ -15,7 +15,7 @@ def rules_python_repository(
         rules_python commit listed in
         drake/tools/install/bazel/test/drake_bazel_installed_test.py.
         """,
-        commit = "0.24.0",
-        sha256 = "0a8003b044294d7840ac7d9d73eef05d6ceb682d7516781a4ec62eeb34702578",  # noqa
+        commit = "0.25.0",
+        sha256 = "5868e73107a8e85d8f323806e60cad7283f34b32163ea6ff1020cf27abef6036",  # noqa
         mirrors = mirrors,
     )
diff --git a/tools/workspace/tinyobjloader_internal/repository.bzl b/tools/workspace/tinyobjloader_internal/repository.bzl
index 283c8985401b..06aa3c171ede 100644
--- a/tools/workspace/tinyobjloader_internal/repository.bzl
+++ b/tools/workspace/tinyobjloader_internal/repository.bzl
@@ -6,8 +6,8 @@ def tinyobjloader_internal_repository(
     github_archive(
         name = name,
         repository = "tinyobjloader/tinyobjloader",
-        commit = "f5569db1ffb3b0222663ba38a7a9b3f6a461c469",
-        sha256 = "f0a0f5ee4e1c7cc573fba9044c1dbed2f547b3ff058840fc8f83c6b7b79f2391",  # noqa
+        commit = "ee45fb41db95bf9563f2a41bc63adfa18475c2ee",
+        sha256 = "10347059b35739d13b37ea40febc38dfe1c482e623026ee35771ab08c3e03883",  # noqa
         build_file = ":package.BUILD.bazel",
         mirrors = mirrors,
         patches = [