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5 results for MIDDLEMAN from Modern Era puzzles:

Repeated clues show (number of Modern Era occurrences).

Date	Grid	Clue	Author
Wed Jul 3, 2019	37A	Go-between (2)	Evan Mahnken
Thu Jan 29, 2015	58A	See 17-Across	John Farmer
Thu Apr 18, 2013	16A	Go-between (2)	Stu Ockman
Wed Jun 27, 2007	34A	Go-between, and a clue to 17-, 24-, 49- and 57-Across	Barbara Olson
Fri May 26, 1995	17A	Broker	Randolph Ross

11 results for MIDDLEMAN from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Mon Dec 7, 1992	57A	Intermediary	Jeff Herrington	Maleska
Wed Apr 6, 1988	21A	Intermediary	Emory H. Cain	Maleska
Sun Jun 14, 1970	49A	Go-between	William Lutwiniak	Weng
Sat Jul 27, 1968	11D	Agent.	Unknown	Farrar
Mon Mar 22, 1965	34D	Go-between.	Unknown	Farrar
Tue Sep 17, 1963	3D	Agent.	Unknown	Farrar
Fri Mar 24, 1961	62A	Trader of a sort.	Unknown	Farrar
Tue Jul 21, 1959	32A	Broker.	Louis Sabin	Farrar
Tue Jul 26, 1955	33D	Go-between.	Fred C. Jaschob	Farrar
Sun Jun 26, 1955	54D	Minstrel show interlocutor.	Harold D. Cannon	Farrar
Sun Dec 19, 1943	84A	Fellow between wholesaler and retailer.	Jack Luzzatto	Farrar

Anagram:

20 ms