John Terry is set to part with some of the most emotionally charged items of his storied Chelsea career, including the infamous “tear-stained” shirt from the 2008 Champions League final defeat to Manchester United. The former Blues captain will auction the memorabilia at a charity sale, with proceeds supporting causes close to his heart through his foundation.Terry has confirmed plans to auction a remarkable collection of personal football memorabilia, headlined by two iconic shirts from his Champions League final appearances with Chelsea. Among the items is the shirt he wore during the 2008 Champions League final loss to Manchester United in Moscow, a match remembered for Terry’s missed penalty in the shootout after slipping on the spot.The former England defender is also selling the full Chelsea kit he wore during the club’s 2012 Champions League triumph over Bayern Munich. Despite being suspended for the final, Terry famously changed into his full playing kit to lift the trophy alongside his teammates, creating one of the most debated images in modern football history.The sale forms part of a 26-lot charity auction being hosted by Goldin Auctions in New Jersey. Proceeds from the event will go to the John Terry Foundation, which supports a range of British charities, with the auction scheduled to conclude on December 31.Explaining the motivation behind the sale, Terry stressed that the decision was driven by charity rather than sentimentality. “My foundation is going to benefit with two close-to-my-heart charities which desperately need the money, so it is going to a great cause,” he said.The former Chelsea skipper acknowledged the emotional weight attached to several of the items, particularly those linked to defining moments of both heartbreak and triumph in his career. The 2008 shirt, which he has described as “tear-stained,” remains one of the most painful reminders of his playing days, while the 2012 kit represents ultimate redemption on Europe’s biggest stage.Terry has also spoken previously about wanting his memorabilia to serve a purpose beyond personal nostalgia. By releasing them into public ownership, he hopes they will raise significant funds while allowing fans and collectors to own tangible pieces of football history tied to Chelsea’s golden era.Looking for smarter football bets? Get expert previews, data-driven predictions & winning insights with GOAL Tips on Telegram. Join our growing community now!The most valuable item in the auction is not a shirt, but Terry’s Premier League winner’s medal from the 2004-05 season. That campaign saw Chelsea secure their first league title in 50 years, with Terry lifting the trophy as captain. The medal alone is expected to fetch up to £75,000, underlining its historical significance.Other notable lots include match-worn shirts swapped with some of the game’s greatest players. Jerseys belonging to Cristiano Ronaldo and Lionel Messi are both included, alongside a shirt from Thierry Henry dating back to Arsenal’s 2003-04 “Invincibles” season. Each item reflects Terry’s longevity and the calibre of opponents he faced throughout his career.The Champions League memorabilia carries particular resonance. The Moscow final shirt from 2008, estimated at £3,750, captures one of the most dramatic nights in European football, while the miniature Champions League trophy from 2012 and the full-kit celebration shirt highlight the emotional extremes Terry experienced at the highest level.Add GOAL.com as a preferred source on Google to see more of our reportingWith the auction set to close on December 31, attention will turn to how much the collection raises for the John Terry Foundation. Given the historic value of the items and Terry’s status as one of Chelsea’s greatest-ever players, the sale is expected to generate significant interest from collectors worldwide.Beyond the auction, Terry continues to focus on his charitable work, using his profile and legacy to support causes across England and Wales. The decision to part with such personal items suggests a conscious effort to turn career-defining moments into lasting positive impact off the pitch.