In February 2002, he moved to Bradford City on a free transfer, aiming to rebuild confidence under Bryan Robson. Though injuries persisted, he managed 52 league appearances over two seasons and scored five goals. In mid-2004, with Bradford relegated and the squad being overhauled, Cadamarteri was released and swiftly signed by Leeds United in June 2004 on a free transfer — a local lad's chance to resurrect his career at Elland Road.

Arriving under Kevin Blackwell's early reign in the Championship, Cadamarteri saw Elland Road as a dream opportunity. He arrived alongside a dozen free transfers intended to rebuild Leeds after relegation from the Premier League. Cadamarteri himself spoke of a desire to 'resurrect' his career and prove himself fit and committed.

Despite optimism, Cadamarteri's Leeds career lasted just over three months. and his onfield contribution amounted to a single substitute appearance, on 21 September 2004 in the League Cup second round at home to Swindon Town, when he came off the bench for Julian Joachim in a 1-0 win. He never played again for Leeds before departing at the end of September.

Local fans expressed early scepticism. Though Cadamarteri claimed upon arrival that he felt fully fit and hungry to fight for his place, his reserve displays weren't enough to break into Blackwell's evolving plans. Within weeks the club deemed him surplus and cleared the way for younger or more dynamic options.

The reasons for his abrupt exit were several. Competition for places in wide areas was fierce, form and fitness remained uncertain, and Leeds quickly moved on: Cadamarteri publicly told Blackwell to 'F*** off' in a comment that reportedly soured his standing in the dressing room and perhaps sealed his fate, though club management never publicly confirmed the facts.

Cadamarteri told the Yorkshire Post, 'I went to Leeds with high hopes, but it turned out to be very frustrating. I thought I was being brought in as a striker because that is where I had finished last season at Bradford and scored quite a few goals. I see myself as a striker and that is where I wanted to play, but the manager saw me as a winger. I have played out there a few times in my career but that was only ever a makeshift switch due to others being injured. I was disappointed not to get a chance up front and when he brought in another striker in Brett Ormerod then I thought I might have to move on. A lot of people thought I was out of the side due to injury but that was not the case.

'I picked up a few knocks and niggles in pre-season but everyone had those. The manager signed me so I hoped to get a chance but it never came. It is disappointing because I wanted to be part of the Leeds United side that went back up. 'There is so much potential but unfortunately I will not get the chance to help the club recover. I am excited about joining a big club in Sheffield United. Outside the Premiership, Leeds and Sheffield United are two of the biggest clubs. Neil tried to sign me when I was at Everton and again at Bradford when he signed Andy Gray so I am looking forward to playing for him.'

Cadamarteri joined Sheffield United on 30 September 2004 for a fee of around £50,000 — less than a season's wages at Leeds, highlighting how swiftly Leeds turned on the signing. At Bramall Lane he made 14 league starts and seven substitute appearances, scoring once before injuries curtailed his season in March 2005.

Cadamarteri's spell at Leeds is often remembered as a warning tale of chaotic recruitment during the post-Wilkinson collapse — clubs signing young established professionals in hope without coherency. Leeds' 2004 summer saw 14 new signings; four had already left by mid-October, making only two combined appearances.

After leaving Leeds, he landed at Sheffield United, scoring once but again hindered by injuries. In June 2005 he returned to Bradford City, but his form declined, and in 2006 he tested positive for ephedrine, leading to a six-month ban — a episode that severely dented his reputation.

Post-ban, Cadamarteri drifted through multiple clubs including Grays Athletic, Leicester City, Doncaster Rovers (loan), Huddersfield Town (two spells) and Dundee United, where a strong debut earned him SPL Player of the Month in August 2009. His later years saw a modest revival, though chronic injuries limited appearances.