The first sign that Roy Keane was done with Old Trafford and ready for a new challenge came at the end of the 1998/99 season.
He had just led the club to the Treble but he was in no rush to sign a contract extension. There was 12 months to run on his current deal and owing to his influential role in the side, he wanted a significant increase.
At the time, he was earning around £20,000 base per week and because of United’s stringent wage structure, they were baulking at his demands of double that.
In mid-summer, he went public and fronted up about the prospect of walking away.
“If the new contract is not right then I won’t sign it,” he said.
“I won’t undersell myself. I would think that this is my last big contract so it has got to be right. Even though I am United’s captain, have moved into a new house and my family are settled here, I won’t sign a deal I am not happy with.
If it isn’t sorted out I will have to look at the bigger picture and I would be prepared to go. That’s not a threat, that’s just life.”
The biggest concern for United was that Keane could talk to interested parties from January 2000 so they needed to get him locked down before the end of the year.
Of course, Keane and his advisor Michael Kennedy were also acutely aware of this. If United didn’t play ball, they would lose their skipper and leader for free and to a rival club.
Michael Steele
Michael Steele
For quite a few months, there was some shadow boxing.
Before a game against Sheffield Wednesday in August 1999, Ferguson was asked about Keane’s situation.
“The most important thing is for us to find a way of keeping Roy Keane,” he said.
“But I trust him, he is a straight-forward lad and he knows what is right.”
The things he will be looking at are not monetary. I don’t think money has come into it at this moment in time, to be honest with you. The only reason he would want to leave is for the challenge of another league. Maybe he wants a change. Who knows?”
Keane had been monitored by other elite European clubs before.
Prior to moving to United in the summer of 1993, there had been interest from abroad, however vague. Real Madrid, Sevilla, Barcelona and Milan were aware of him and casually keeping an eye. But Keane was younger then and had no interest in making such a dramatic move.
In 1999, it was different.
United had claimed a European Cup but certainly weren’t perennial guests at the competition’s top table. Essentially, they were feeding on scraps. Keane looked at Juventus, Milan, Bayern and Real Madrid and wondered if United would ever be at the same consistent level. Even if Ferguson chose not to accept it as a determining factor, money was important. And none of those teams mentioned had similar wage constraints to United.
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The club hoped that Keane would see sense, accept their offer of around £30,000 per week and reveal the positive news after a weekend clash with Leeds in the third game of the campaign.
Keane did release a statement afterwards but United were in for a surprise.
“At the present time I am undecided as to my future after June of next year,” he said.
“Over the next few months I will give proper and due consideration to the club’s most recent proposal and I shall make a decision concerning my future at the end of this season.”
If anyone thought the ongoing process would affect him or act as a distraction, Keane rubbished such a sentiment. In fact, in United’s next league fixture away to Arsenal, Keane conjured one of his most famous performances. He scored twice, including the 88th-minute winner, as United came from a goal down to produce a firm statement of intent against a side that ran them so close throughout the previous season.
Jed Leicester
Jed Leicester
At this juncture he was magnificent, particularly in Europe. There were goals home and away against Sturm Graz and another against Croatia Zagreb. There was an uncharacteristic error during the next group stage in Florence but, inevitably, Keane followed that by grabbing the winner in the Intercontinental Cup against Palmeiras a week later in Tokyo.
After that game, he spoke to the media again and admitted indecision about his contract. By this stage it was 30 November and there was still no agreement in place.
“To walk away from Manchester United will be a wrench, but I haven’t made my mind up,” Keane said.
“It’s crunch time in the next couple of weeks. Certain people want decisions. I change my mind every day. Winning things like this obviously helps.
Everyone knows I love the club. Sometimes there’s politics involved. The club has been a little bit criticised over the years for being a little bit tight, maybe. I’ve always said I understand the club’s point of view, but hopefully they will understand mine.”
One of the finest midfielders in the world, Keane’s worth was now undeniable and with the clock ticking United’s top brass finally relented. A replacement of a similar calibre would cost upwards of £10m anyway so they agreed to make an exception and loosen the financial reins.
They agreed a new deal with Keane worth £50,000 per week (£40,000 base with some top-ups), making him the club’s highest earner by a distance and keeping him at United until 2003.
Confirmation came on the evening of 7 December, minutes before a crucial Champions League tie with Valencia.
Because of the defeat to Fiorentina, Ferguson had labelled it a must-win game and though the Spaniards were missing some big names due to injury and suspension, they still boasted the likes of Gaizka Mendieta and Claudio Lopez.
As United kicked off, the stadium announcer informed the masses at Old Trafford that their captain was staying put, news greeted with an inevitably boisterous and relieved chorus of ‘Keano, Keano’.
With seven minutes of the first half left, he burst onto a poor clearing header from Amadeo Carboni and drove a low strike to the bottom corner.
Neal Simpson
Neal Simpson
After the initial surge of celebration alongside his team-mates, Keane waited until he was alone, looked to the stands and briefly applauded the supporters. Certainly not the romantic type, even he could still acknowledge just how perfect the timing was.
“It had to be Roy Keane,” said Clive Tyldesley on ITV.
“The perfect day for the Man United captain.”
United went on to win 3-0 and topped that second group stage. But, it was Valencia who went on to reach the decider that year.
In the quarter-finals, United were held scoreless at the Bernabeu. In the return leg, Keane put through his own goal, missed an open goal and saw Fernando Redondo produce one of those special Champions League moments as he set up Raul for his second and Real’s third of the night.
United fought gamely and got it back to 3-2 but it wasn’t enough and they were out. Keane deserved better, having struck six times in the tournament – the same frequency as Gabriel Batistuta and Fernando Morientes.
Mike Egerton
Mike Egerton
Still, he had to make do with lifting another Premier League title as his side cantered to another domestic championship in May. In an unusual turn of events, he even picked up some individual accolades for his superb displays and voted both the PFA Player of the Year and the FWA Player of the Year.
But in Saint-Denis later that month, it was Real who were crowned Champions League winners for the second time in three years.
It was certainly irritating for Keane. The following season, he seemed a ball of frustration. There was the ‘prawn sandwich’ comments that came after a Champions League group game against Dynamo Kiev, general cribbing about the standard of performances after a group-stage draw with Valencia and then a searing analysis of their limitations following another quarter-final elimination, this time against Bayern.
“The players gave it their all tonight but we are just not good enough and maybe it’s time to move on,” he told MUTV.
Maybe it’s the end of the road for this team, although I’m not sure. It’s no good winning the Premier League, we need to step up a level in Europe. I keep going on about Real Madrid but they’re setting the standards we have to match.”
It’s no coincidence that days later, he exploded on the pitch and exacted x-rated revenge on Alf Inge Haaland in the Manchester derby.
A fuming Roy Keane walks off after United are held to a 1-1 draw by Bayer Leverkusen and eliminated on away goals in the semi-finals of the Champions League in 2002. Martin Rickett
Martin Rickett
The following season, United were better and reached the Champions League semi-finals but despite Keane grabbing a crucial away goal in the second-leg against Bayer Leverkusen, they conceded shortly after and went out on away goals. Afterwards, he raged at United’s inability to deliver on the biggest stage once more.
“We blew it,” he said.
This club deserves to win another European Cup and we blew it. It’s as simple as that. We had a great opportunity and these sort of chances don’t come along very often. This club belongs in the European Cup final and it’s a disaster and very disappointing. It’s more disappointing for the manager, the staff and the fans because I think they deserved better than this.”
The following month, it was Real Madrid’s trophy again thanks to Zinedine Zidane’s acrobatic volley at Hamden Park.
“I am absolutely delighted that my future with the best club in the world is now secure,” Keane had said in the official statement that accompanied him signing the new deal in 1999.
“I never wanted to leave Manchester United and the contract that I have now signed indicated to me United’s desire to remain at the top of world football.”
But, there’s always hindsight.
Keane certainly met with Bayern Munich representatives and discussed a potential move. And there was definitely an offer on the table from Juventus too. Later, after leaving United in 2005, there was more interest – this time from Real – though Keane didn’t jump at it and signed for Celtic instead.
“I was 34 and my hip was hurting me,” he said in 2014.
“Maybe I took the easier option by going to Celtic – it was certainly easier on my body. If I had my time over again, then maybe (I’d have gone to Real), but I enjoyed being at Celtic.
“My regret was that I should have gone abroad earlier in my career. I could have signed for Juventus or Bayern Munich – I had much better financial offers from them – but at the time I wanted to stay at United. I felt at home at Old Trafford.”
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'I'd be prepared to go. That's not a threat, it's just life': Old Trafford, Valencia and Roy Keane's 'perfect day'
“It had to be Roy Keane.
The perfect day for the Man United captain.”
IT HAD RUMBLED on for seven months.
The first sign that Roy Keane was done with Old Trafford and ready for a new challenge came at the end of the 1998/99 season.
He had just led the club to the Treble but he was in no rush to sign a contract extension. There was 12 months to run on his current deal and owing to his influential role in the side, he wanted a significant increase.
At the time, he was earning around £20,000 base per week and because of United’s stringent wage structure, they were baulking at his demands of double that.
In mid-summer, he went public and fronted up about the prospect of walking away.
“If the new contract is not right then I won’t sign it,” he said.
“I won’t undersell myself. I would think that this is my last big contract so it has got to be right. Even though I am United’s captain, have moved into a new house and my family are settled here, I won’t sign a deal I am not happy with.
The biggest concern for United was that Keane could talk to interested parties from January 2000 so they needed to get him locked down before the end of the year.
Of course, Keane and his advisor Michael Kennedy were also acutely aware of this. If United didn’t play ball, they would lose their skipper and leader for free and to a rival club.
For quite a few months, there was some shadow boxing.
Before a game against Sheffield Wednesday in August 1999, Ferguson was asked about Keane’s situation.
“The most important thing is for us to find a way of keeping Roy Keane,” he said.
“But I trust him, he is a straight-forward lad and he knows what is right.”
Keane had been monitored by other elite European clubs before.
Prior to moving to United in the summer of 1993, there had been interest from abroad, however vague. Real Madrid, Sevilla, Barcelona and Milan were aware of him and casually keeping an eye. But Keane was younger then and had no interest in making such a dramatic move.
In 1999, it was different.
United had claimed a European Cup but certainly weren’t perennial guests at the competition’s top table. Essentially, they were feeding on scraps. Keane looked at Juventus, Milan, Bayern and Real Madrid and wondered if United would ever be at the same consistent level. Even if Ferguson chose not to accept it as a determining factor, money was important. And none of those teams mentioned had similar wage constraints to United.
The club hoped that Keane would see sense, accept their offer of around £30,000 per week and reveal the positive news after a weekend clash with Leeds in the third game of the campaign.
Keane did release a statement afterwards but United were in for a surprise.
“At the present time I am undecided as to my future after June of next year,” he said.
“Over the next few months I will give proper and due consideration to the club’s most recent proposal and I shall make a decision concerning my future at the end of this season.”
If anyone thought the ongoing process would affect him or act as a distraction, Keane rubbished such a sentiment. In fact, in United’s next league fixture away to Arsenal, Keane conjured one of his most famous performances. He scored twice, including the 88th-minute winner, as United came from a goal down to produce a firm statement of intent against a side that ran them so close throughout the previous season.
At this juncture he was magnificent, particularly in Europe. There were goals home and away against Sturm Graz and another against Croatia Zagreb. There was an uncharacteristic error during the next group stage in Florence but, inevitably, Keane followed that by grabbing the winner in the Intercontinental Cup against Palmeiras a week later in Tokyo.
After that game, he spoke to the media again and admitted indecision about his contract. By this stage it was 30 November and there was still no agreement in place.
“To walk away from Manchester United will be a wrench, but I haven’t made my mind up,” Keane said.
“It’s crunch time in the next couple of weeks. Certain people want decisions. I change my mind every day. Winning things like this obviously helps.
One of the finest midfielders in the world, Keane’s worth was now undeniable and with the clock ticking United’s top brass finally relented. A replacement of a similar calibre would cost upwards of £10m anyway so they agreed to make an exception and loosen the financial reins.
They agreed a new deal with Keane worth £50,000 per week (£40,000 base with some top-ups), making him the club’s highest earner by a distance and keeping him at United until 2003.
Confirmation came on the evening of 7 December, minutes before a crucial Champions League tie with Valencia.
Because of the defeat to Fiorentina, Ferguson had labelled it a must-win game and though the Spaniards were missing some big names due to injury and suspension, they still boasted the likes of Gaizka Mendieta and Claudio Lopez.
As United kicked off, the stadium announcer informed the masses at Old Trafford that their captain was staying put, news greeted with an inevitably boisterous and relieved chorus of ‘Keano, Keano’.
With seven minutes of the first half left, he burst onto a poor clearing header from Amadeo Carboni and drove a low strike to the bottom corner.
After the initial surge of celebration alongside his team-mates, Keane waited until he was alone, looked to the stands and briefly applauded the supporters. Certainly not the romantic type, even he could still acknowledge just how perfect the timing was.
“It had to be Roy Keane,” said Clive Tyldesley on ITV.
“The perfect day for the Man United captain.”
United went on to win 3-0 and topped that second group stage. But, it was Valencia who went on to reach the decider that year.
In the quarter-finals, United were held scoreless at the Bernabeu. In the return leg, Keane put through his own goal, missed an open goal and saw Fernando Redondo produce one of those special Champions League moments as he set up Raul for his second and Real’s third of the night.
United fought gamely and got it back to 3-2 but it wasn’t enough and they were out. Keane deserved better, having struck six times in the tournament – the same frequency as Gabriel Batistuta and Fernando Morientes.
Still, he had to make do with lifting another Premier League title as his side cantered to another domestic championship in May. In an unusual turn of events, he even picked up some individual accolades for his superb displays and voted both the PFA Player of the Year and the FWA Player of the Year.
But in Saint-Denis later that month, it was Real who were crowned Champions League winners for the second time in three years.
It was certainly irritating for Keane. The following season, he seemed a ball of frustration. There was the ‘prawn sandwich’ comments that came after a Champions League group game against Dynamo Kiev, general cribbing about the standard of performances after a group-stage draw with Valencia and then a searing analysis of their limitations following another quarter-final elimination, this time against Bayern.
“The players gave it their all tonight but we are just not good enough and maybe it’s time to move on,” he told MUTV.
It’s no coincidence that days later, he exploded on the pitch and exacted x-rated revenge on Alf Inge Haaland in the Manchester derby.
The following season, United were better and reached the Champions League semi-finals but despite Keane grabbing a crucial away goal in the second-leg against Bayer Leverkusen, they conceded shortly after and went out on away goals. Afterwards, he raged at United’s inability to deliver on the biggest stage once more.
“We blew it,” he said.
The following month, it was Real Madrid’s trophy again thanks to Zinedine Zidane’s acrobatic volley at Hamden Park.
“I am absolutely delighted that my future with the best club in the world is now secure,” Keane had said in the official statement that accompanied him signing the new deal in 1999.
“I never wanted to leave Manchester United and the contract that I have now signed indicated to me United’s desire to remain at the top of world football.”
But, there’s always hindsight.
Keane certainly met with Bayern Munich representatives and discussed a potential move. And there was definitely an offer on the table from Juventus too. Later, after leaving United in 2005, there was more interest – this time from Real – though Keane didn’t jump at it and signed for Celtic instead.
“I was 34 and my hip was hurting me,” he said in 2014.
“Maybe I took the easier option by going to Celtic – it was certainly easier on my body. If I had my time over again, then maybe (I’d have gone to Real), but I enjoyed being at Celtic.
“My regret was that I should have gone abroad earlier in my career. I could have signed for Juventus or Bayern Munich – I had much better financial offers from them – but at the time I wanted to stay at United. I felt at home at Old Trafford.”
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UEFA Champions League Roy Keane Manchester United Valencia what if