diff --git a/typed-racket-lib/typed-racket/private/type-contract.rkt b/typed-racket-lib/typed-racket/private/type-contract.rkt
index 54e78552..ba2e50dd 100644
--- a/typed-racket-lib/typed-racket/private/type-contract.rkt
+++ b/typed-racket-lib/typed-racket/private/type-contract.rkt
@@ -627,6 +627,9 @@
          (syntax/sc (t->sc t))]
         [(Value: v)
          (if (and (c:flat-contract? v)
+                  ;; numbers used as contracts compare with =, but TR
+                  ;; requires an equal? check
+                  (not (number? v))
                   ;; regexps don't match themselves when used as contracts
                   (not (regexp? v)))
              (flat/sc #`(quote #,v))
diff --git a/typed-racket-test/unit-tests/contract-tests.rkt b/typed-racket-test/unit-tests/contract-tests.rkt
index a040645e..ba0267c3 100644
--- a/typed-racket-test/unit-tests/contract-tests.rkt
+++ b/typed-racket-test/unit-tests/contract-tests.rkt
@@ -368,6 +368,18 @@
                           #:untyped
                           #:msg #rx"that accepts 1 non-keyword")
 
+              ;; Value types with numbers shouldn't be checked with =
+              (t-int/fail (make-Value 3.0)
+                          values
+                          3
+                          #:untyped
+                          #:msg #rx"promised: 3.0")
+              (t-int/fail (make-Value 3)
+                          values
+                          3.0
+                          #:untyped
+                          #:msg #rx"promised: 3")
+
               ;; intersection types
               (t (-unsafe-intersect (-seq -Symbol) (-pair -Symbol (-lst -Symbol))))
               (t/fail (-unsafe-intersect (-Number . -> . -Number) (-String . -> . -String))