Former Liverpool manager says failure to sign Teddy Sheringham was his “biggest transfer regret”

"They thought at the age of twenty-seven or whatever it was that he was too old."

Teddy Sheringham could have ended up at Anfield instead of Old Trafford. In 1997, the former England international left Tottenham Hotspur for Premier League champions Manchester United in a transfer worth £3.5m. He was tasked with replacing United legend Eric Cantona, who had just retired, and while he didn't have the same impact as the Frenchman at Old Trafford, Sheringham would prove a very shrewd signing. The forward helped Sir Alex Ferguson's side to three league titles in four years, the FA Cup and the Champions League in 1999. He scored the team's injury-time equaliser in the Champions League final against Bayern Munich, before heading the ball onto Ole Gunnar Solskjaer's foot to win the trophy a minute later. However, if Liverpool had signed Sheringham a few seasons earlier, United's greatest victory would not have played out as it did. According to Roy Evans, Liverpool manager between 1994 and 1998, the forward was keen on a move to Anfield, but the club's board at the time wouldn't sanction the transfer. They considered a 27-year-old Sheringham to be "too old" to have any potential re-sale value.   "Biggest transfer regret? I'd say Teddy Sheringham," Evans told The Liverpool Way.

"It was a boardroom decision not to sign him because of his age. They thought at the age of twenty-seven or whatever it was that he was too old. Not too old to play, but too old to be a good investment. He went on to play a number of years with Manchester United, and then back to Tottenham and was very successful. I spoke to Teddy before that, and since then, and he wanted to come, it was just a boardroom decision and as a manager you just have to take that. It was a fair answer, they just felt it wasn’t right. Although they were proved wrong by how Teddy played for United. You just take that on the chin though."

Sheringham joined United when he was 31 and played in the Premier League until he was 41. At 27, he would have been a brilliant strike-partner for Robbie Fowler at Liverpool and proved a great signing for Ferguson.