===Coventry City===
I juli 1983 vendte han tilbage til førstedivisionen, da han skiftede til [[Coventry City F.C.|Coventry City]]. Det blev fulgt at fem stærke sæsoner, hvor klubben [[FA Cup Finalen 1987|vandt pokalfinalen i 1987]]. Bennet scorede Coventrys første mål og lagde op til [[Keith Houchen]] mål senere i kampen, som sluttede med den noget overraskende sejr på 3-2 over [[Tottenham Hotspur F.C.|Tottenham Hotspur]] på [[Wembley Stadium|Wembley]].<ref>{{cite web |url=http://www.dailymail.co.uk/sport/football/article-1160072/Sky-Blue-army-Coventry-Citys-FA-Cup-heroes-now.html |title=Sky Blue army: where are Coventry City's FA Cup heroes now? |publisher=Daily Mail |date=6. marts 2009 |accessdate=10. juni 2016 |archive-date=20. august 2016 |archive-url=https://web.archive.org/web/20160820082704/http://www.dailymail.co.uk/sport/football/article-1160072/Sky-Blue-army-Coventry-Citys-FA-Cup-heroes-now.html |url-status=ok }}</ref> Coventry had gone into the match as underdogs but Bennett later stated: "The critics say we were the underdogs because Tottenham had all these international players [...] but we weren't afraid of them.<ref>{{cite web |url=http://coventryobserver.co.uk/sport/sky-blues-1987-fa-cup-anniversary-look-back-players-coaches-said/ |title=Sky Blues 1987 FA Cup anniversary – A look back at what the players and coaches said |publisher=Coventry Observer |date=16. maj 2016 |accessdate=10. juni 2016 |archive-date=13. juni 2018 |archive-url=https://web.archive.org/web/20180613235208/https://coventryobserver.co.uk/sport/sky-blues-1987-fa-cup-anniversary-look-back-players-coaches-said/ |url-status=ok }}</ref>
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