In 1997, Festa joined Middlesbrough, being one of the first Italians to play in the Premier League. Festa arrived at Middlesbrough from Inter Milan in the midst of a relegation battle to add steel to the defence. Festa was the second Italian at the club with Middlesbrough also having Italian International Fabrizio Ravanelli at the club. Festa scored on an impressive winning debut against Sheffield Wednesday in January 1997. Festa had been an accomplished martial arts master, a junior Italian tennis champion and captain of the Army team when he did his national service. He had shrewd positional sense, was tough in the tackle, a dominating figure in the air and got forward on occasions to score the odd important goal. After scoring in the semi final against Chesterfield, a goal that could have been even more historic was ruled out when Festa's header in the 1997 FA Cup Final was deemed offside. That was one of three Wembley appearances he made in his first 18 months at the club.