As the 1999/2000 season came to a close, Jimmy Brennan sat back and weighed up what had been an impressive debut campaign with Nottingham Forest. He'd only arrived in October from Bristol City but still racked up 27 league appearances under manager David Platt.

A decent beginning.

He'd go on to enjoy three more fulsome years at the City Ground but had circumstances played out differently, Brennan could have - rather incredibly - found himself at the centre of one of Spanish football's greatest moments instead.

"It was funny how it worked out," he begins.

"When I was sold to Nottingham Forest, I actually thought I was going to Deportivo La Coruna in La Liga. They had been watching our centre-back, Vilmos Sebok, who was a Hungarian international. The videos were sent over and I must have had a couple of good games. They ended up sending the scouts across to watch Vilmos and me and then my agent said, 'Look, they're coming after you'. They were preparing an offer but then I remember getting a call at 11.30pm from the chairman of Bristol who said, 'Forest have put a bid in, we've accepted and you're going to them'.

"Now, I absolutely loved it there. The history is just incredible. Brian Clough would come to quite a few of our games, the European Cup winners were always walking around, when you arrived at the City Ground you'd go right past the trophy cabinets. There's so much pride in the place and I loved every minute that I played for them. I represented them almost 150 times. It was a great period and a good move for me personally and as a footballer. I wanted to play in the Premier League and they'd just dropped down but were pushing to get back up. It was a big club and they had a good squad under David Platt."

While Brennan nestled deep into the Forest, Javier Irureta was creating a quiet revolution in Spain with Deportivo. Historically unfashionable, the club had only been back in the top-flight for nine years when the miracle occurred. From the previous fifteen editions of the championship, only Atleti (in 1996) managed to break the duopoly of Barcelona and Real Madrid. In previous seasons, Deportivo had got close, particularly in 1994 when a missed penalty on the last day cost them a title. But as the new Millennium dawned, they started to build momentum and never looked back.

With Dutch summer signing Roy Makaay contributing 22 league goals, the magnificent Brazilian midfielder Djalminha excelling, his compatriot Mauro Silva a consistently solid presence and Fran a dependable skipper, Irureta assembled a finely-balanced side. At the back, they were equally adept with Moroccan centre-half Noureddine Naybet (later to play alongside York United FC assistant coach Paul Stalteri at Tottenham Hotspur) perfectly complemented by the ageless Donato.

On May 19, they beat Espanyol at home and were crowned champions. Though it remains their only La Liga success, it ensured a place at Europe's top table and throughout the next few years, Deportivo were a celebrated tour-de-force in the Uefa Champions League, their consistency culminating in a run to the semi-finals in 2004, where they narrowly fell to a 1-0 aggregate defeat to Jose Mourinho's eventual winners FC Porto.

By that stage, Brennan had swapped Nottingham for Norwich, a move that saw him finally live out his dream of being a Premier League footballer.

"The Forest chairman wanted to control the budget a little bit more and we ended up losing about a dozen players within a year or two and all of them ended up playing in the Premier League," Brennan says.

"I got a call from Nigel Worthington and he said, 'Here's the plan, here are the guys I'm going after and we're getting promoted'. Norwich are a yo-yo club but I felt it was a perfect move. I flew over from Toronto to sign the contract at Carrow Road and, sure enough, we ended up being promoted."

Prior to his move to Toronto FC in 2007, Brennan had one more experience of the often-chaotic transfer window. The previous year, he eventually signed for Southampton, though they weren't always at the top of the queue.

"There were a few clubs sniffing around and I thought I might be going to Middlesbrough at one point," he says.

"But there could be a call from anybody. You know what the tabloids are like and you're watching BBC Sport and reading the newspapers and they've got all the gossip about who's watching you. And then you're just waiting for the call."

"George Burley was in charge of Southampton at the time and he said, 'Okay Jimmy, let's go. I want to bring you in and let's see how things progress.' So I ended up signing and I really enjoyed my time there. Later, when we were discussing contracts, Toronto FC and MLSE came in and said, 'We want to bring you back home.' I was 29 and wanted to play in front of my friends and family because they never really got to see me too much. They watched on TV but never really could come over, except around Christmas time. So it was the right move at the right time."

And no regrets over missing out on a reign in Spain?

"Absolutely not," he says, defiantly.

"Y'know, you hear that you might be going to La Liga and it's exciting but I was young at the time too. You never know how a move like that will play out. And I loved English football. I was watching the Premier League every weekend. And that was always the big draw for me."

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