diff --git a/pex/bin/pex.py b/pex/bin/pex.py
index c0634f197..23d584f1d 100755
--- a/pex/bin/pex.py
+++ b/pex/bin/pex.py
@@ -526,22 +526,6 @@ def configure_clp_pex_environment(parser):
         "distributions can be found.",
     )
 
-    group.add_option(
-        "--use-first-matching-interpreter",
-        dest="use_first_matching_interpreter",
-        default=False,
-        action="callback",
-        callback=parse_bool,
-        help=(
-            "If multiple interpreters are valid, use the first one, which is the minimum "
-            "compatible Python version. Normally, when multiple interpreters match, Pex will "
-            "resolve requirements for each interpreter; this allows the resulting Pex to be "
-            "compatible with more interpreters, such as different Python versions. However, "
-            "resolving for multiple interpreters will take longer to build, and the resulting PEX "
-            "may be larger."
-        ),
-    )
-
     parser.add_option_group(group)
 
 
@@ -803,18 +787,6 @@ def to_python_interpreter(full_path_or_basename):
             )
 
     interpreter = min(interpreters) if interpreters else None
-    if options.use_first_matching_interpreter and interpreters:
-        if len(interpreters) > 1:
-            unused_interpreters = set(interpreters) - {interpreter}
-            TRACER.log(
-                "Multiple interpreters resolved, but only using {} because "
-                "`--use-first-matching-interpreter` was used. These interpreters were matched but "
-                "will not be used: {}".format(
-                    interpreter.binary,
-                    ", ".join(interpreter.binary for interpreter in sorted(unused_interpreters)),
-                )
-            )
-        interpreters = [interpreter]
 
     try:
         with open(options.preamble_file) as preamble_fd:
@@ -850,16 +822,7 @@ def walk_and_do(fn, src_dir):
     pex_info.pex_root = options.runtime_pex_root
     pex_info.strip_pex_env = options.strip_pex_env
 
-    # If we're only building the PEX for the first of many interpreters due to
-    # `--use-first-matching-interpreter` selection, we do not want to enable those same interpreter
-    # constraints at runtime, where they could lead to a different interpreter being selected
-    # leading to a failure to execute the PEX. Instead we rely on the shebang set by that single
-    # interpreter to pick out a similar interpreter at runtime (for a CPython interpreter, the
-    # shebang will be `#!/usr/bin/env pythonX.Y` which should generally be enough to select a
-    # matching interpreter. To be clear though, there are many corners this will not work for
-    # including mismatching abi (python2.7m vs python2.7mu) when the PEX contains platform specific
-    # wheels, etc.
-    if options.interpreter_constraint and not options.use_first_matching_interpreter:
+    if options.interpreter_constraint:
         for ic in options.interpreter_constraint:
             pex_builder.add_interpreter_constraint(ic)
 
diff --git a/tests/test_integration.py b/tests/test_integration.py
index 6dd1ee631..1d84721f5 100644
--- a/tests/test_integration.py
+++ b/tests/test_integration.py
@@ -619,53 +619,6 @@ def test_interpreter_resolution_pex_python_path_precedence_over_pex_python():
         assert correct_interpreter_path in stdout
 
 
-def test_use_first_matching_interpreter():
-    # type: () -> None
-    py35_path = ensure_python_interpreter(PY35)
-    py36_path = ensure_python_interpreter(PY36)
-    env = make_env(PEX_PYTHON_PATH=os.pathsep.join((py35_path, py36_path)))
-
-    def run_pex_with_py36(use_first_matching_flag):
-        with temporary_dir() as output_dir:
-            pex_out_path = os.path.join(output_dir, "first_matching.pex")
-            args = [
-                "--disable-cache",
-                "--interpreter-constraint=>=3.5",
-                "-o",
-                pex_out_path,
-                "psutil==5.7.0",
-            ]
-            if use_first_matching_flag:
-                args.append("--use-first-matching-interpreter")
-            res = run_pex_command(args, env=env)
-            res.assert_success()
-
-            pex_info = PexInfo.from_pex(pex_out_path)
-            assert (
-                [] if use_first_matching_flag else [">=3.5"]
-            ) == pex_info.interpreter_constraints
-
-            # Running with Python 3.5 should always work because that is the first matching
-            # interpreter.
-            stdin_payload = b"import sys, psutil; print(sys.executable); sys.exit(0)"
-            stdout, rc = run_simple_pex(pex_out_path, stdin=stdin_payload, env=env)
-            assert rc == 0
-            assert py35_path in stdout.decode()
-
-            stdout, rc = run_simple_pex(
-                pex_out_path, stdin=stdin_payload, env=make_env(PEX_PYTHON_PATH=py36_path)
-            )
-            return stdout, rc
-
-    without_flag_stdout, without_flag_rc = run_pex_with_py36(use_first_matching_flag=False)
-    assert without_flag_rc == 0
-    assert py36_path in without_flag_stdout.decode()
-
-    with_flag_stdout, with_flag_rc = run_pex_with_py36(use_first_matching_flag=True)
-    assert with_flag_rc == 1
-    assert bool(re.search(r"Needed.*cp-36-cp36m", with_flag_stdout.decode()))
-
-
 def test_plain_pex_exec_no_ppp_no_pp_no_constraints():
     # type: () -> None
     with temporary_dir() as td: