Date: 7th August 2009 at 7:34pm
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Leaving aside the arrival of the great Colin Stein in the 1970’s, Coventry City’s transfer dealings with Glasgow Rangers have invariably benefitted the Scottish giants, with the late 1980’s and early 1990’s seeing a series of disastrous deals done by the Sky Blues.

Kevin Drinkell’s arrival for a club record £800,000, early in the 1989/90 season was seen at the time (can you believe?) as the missing piece of a title-winning jigsaw at Highfield Road.

He made a promising early impact and scored a cracking goal against Aston Villa live on TV but after that it went downhill rapidly.

Drinkell disappeared from view under one of his former Ibrox team-mates, Terry Butcher, who replaced the sacked John Sillett late in 1990.

Butcher, it could be argued got a raw deal and very little time in his first managerial role and certainly made some decent signings.

However, as well as his manager’s salary, City had paid £400,000 for the ex-England captain’s playing registration.

Time had taken its toll on the warhorse centre-half and Butcher was all at sea on his return to the English top-flight, making only a few appearances before hanging up his boots.

Next to travel down from Glasgow to Coventry was midfielder Sandy Robertson, who had two main problems to contend with.

Firstly he was way out of his depth in English football and secondly he was signed to replace Chris Marsden, who had dazzled on loan from Huddersfield but hadn’t been signed permanently.

Then in 1994, the Sky Blues spent £650,000 of the money received from the sale of Phil Babb on Rangers’ youngster Steven Pressley.

Pressley’s subsequent sterling service to the likes of Dundee United and Hearts showed what a good player he was but the move south had come far too early and being thrown in at the deep end gave him no time at all to adjust.