A repro:
#lang typed/racket/base
(: f11 (-> (Listof Real) (Listof Real)))
(define (f11 rs)
(map (lambda (z) (assert-typecheck-fail (+ z 5.0) #:result (error 'a))) rs))
../../Applications/Racket9.0/share/pkgs/typed-racket-lib/typed-racket/types/tc-result.rkt:226:2: match: no matching clause for #f
A repro: