Middlesbrough boss warns Leicester City after Gaston Ramirez hands in transfer request

Karanka confirmed that the 26-year-old Uruguay international has handed in a transfer request, and that the Foxes have had a bid for his services rejected as he faces a battle to hang on to a man the Teessiders worked hard to sign on a permanent basis during the summer.

Karanka said: "Yes, he's handed in a transfer request, but the offer that we received is not good enough.

"It's more than difficult, it's frustrating because he was calling us to play here last season.

"He played his best last season, he went back to the national team again playing with us and to have this situation is frustrating as a coach and as a person."

Leicester boss Claudio Ranieri was coy when asked a bout the situation at his pre-match press conference.

The Italian said: "This is not my matter. I am head coach, I am not manager. I don't speak about money."

Karanka found himself in a similar position last season when now Aston Villa midfielder Albert Adomah asked to leave the club, and while he has admitted he feels let down by Ramirez, he believes the damage is not irreparable.

He said: "We have a really good example with Albert. I don't know how many times there were rumours that I had a really, really bad relationship with Albert, but the first day he played, he scored and he came to me to give me a hug."

Karanka also confirmed that Boro have had a bid for Hull's Robert Snodgrass rejected with Burnley and West Ham also vying for the services of the £10million-rated Scotland international.

Asked if he felt the Tigers were reluctant to do business with a potential relegation rival, he replied: "You don't need to go to university to know that, it's obvious.

"He's a player who we like, he's a player who we are trying to bring here and let's see. We have four or five days to see what is happening."

Snodgrass is one of a series of targets for Karanka, who has already added Rudy Gestede and Patrick Bamford to his squad this month, and he has confirmed his interest in Paris St Germain's Jese Rodriguez, with whom he has worked within the Spain youth set-up and Real Madrid.

He said: "It's massive because he's a player who I have known for the last seven, eight years.

"He was one of my favourite players when he was in the national team. I was with him when I was at Real Madrid, I know his potential, I know his character, so he could help us a lot.

"PSG paid this summer 25million Euros for him, so he's a player who can bring us a lot of things, and we are trying to convince him."