The Scotland international was a title winner with Celtic in 2008, and spent two years at Parkhead before he was signed by former boss Gordon Strachan at Middlesbrough for a fee of a fee of £1million. Remember on Teesside for a series of long-range goals, he was named their player of the year in 2012, before moving to the MLS with Vancouver Whitecaps. Ended his career in 2016, and has since gone into management, taking charge of both Raith Rovers and former club Aberdeen. He currently manages League of Ireland club Cork City.placeholder image
The Scotland international was a title winner with Celtic in 2008, and spent two years at Parkhead before he was signed by former boss Gordon Strachan at Middlesbrough for a fee of a fee of £1million. Remember on Teesside for a series of long-range goals, he was named their player of the year in 2012, before moving to the MLS with Vancouver Whitecaps. Ended his career in 2016, and has since gone into management, taking charge of both Raith Rovers and former club Aberdeen. He currently manages League of Ireland club Cork City. | Getty Images

Celtic vs Middlesbrough: 11 players who played for both clubs - including £25m ace, major flop and cherished midfielder

By Graham Falk

Sports Writer

Published 17th Jul 2026, 16:45 BST

Here are 11 players to have played for both Celtic and Middlesbrough ahead of the club’s pre-season friendly at Parkhead this weekend.

Celtic’s pre-season continues to gather pace this weekend as they welcome EFL Championship outfit Middlesbrough to Parkhead for a 3pm kick-off on Saturday.

Martin O’Neill’s side have yet to taste victory in their first two warm-up games, drawing 1-1 with Shelbourne before losing 4-1 to Sporting CP in Portugal on Tuesday night, and will be looking to ramp up their preparations with a victory on home soil against Kim Hellberg’s visiting Teessiders.

Believe it or not, Celtic and Middlesbrough have not seen a senior player transfer between the clubs since 2010, although Hoops academy product Josh Dede did move to the Riverside Stadium in January of 2025, but has yet to feature in the first team.

In truth, the success rate of players transferred between the club ranges from the sublime to the ridiculous, with club legends, major flops and forgotten talents all included.

But can you remember these 11 players who have played for both clubs?

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The defender took over the armband from Neil Lennon in 2007 and went on to lead Celtic to the Scottish Premiership title. Won seven trophies during his time in Glasgow, and is perhaps best remembered for his dramatic late double against Hearts on New Year's Day in 2006, where his two late goals secured a 3-2 comeback victory. Moved on loan to Middlesbrough in 2010, originally on loan, but was troubled by injury, before he returned to Scotland with Motherwell. Retired in 2017.

9. Stephen McManus

The defender took over the armband from Neil Lennon in 2007 and went on to lead Celtic to the Scottish Premiership title. Won seven trophies during his time in Glasgow, and is perhaps best remembered for his dramatic late double against Hearts on New Year's Day in 2006, where his two late goals secured a 3-2 comeback victory. Moved on loan to Middlesbrough in 2010, originally on loan, but was troubled by injury, before he returned to Scotland with Motherwell. Retired in 2017. | Getty Images Photo: Getty Images

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A product of the Celtic academy, Whyte made his debut for the club aged just 17, and went on to win two leagues and two Scottish Cups over an eight-year period at Parkhead. Sold to Middlesbrough for a fee of £900,000 in 1992, he helped the Teessiders win promotion to the English Premier League as champions under manager Bryan Robson in 1995. Part of the Scotland squad at Euro 1992, Euro 1996 and the 1998 World Cup, he retired in 2004 after a two-year stint at Partick Thistle.

10. Derek Whyte

A product of the Celtic academy, Whyte made his debut for the club aged just 17, and went on to win two leagues and two Scottish Cups over an eight-year period at Parkhead. Sold to Middlesbrough for a fee of £900,000 in 1992, he helped the Teessiders win promotion to the English Premier League as champions under manager Bryan Robson in 1995. Part of the Scotland squad at Euro 1992, Euro 1996 and the 1998 World Cup, he retired in 2004 after a two-year stint at Partick Thistle. | SNS Group 0141 221 3602 Photo: SNS Group 0141 221 3602

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The most recent name to play for both clubs, Gannon-Doak, began his career in the Celtic academy, making his debut as a late substitute in a clash with Dundee United at just 16. Snapped up by Liverpool shortly afterwards, he had his first real taste of regular football on loan to Middlesbrough in the 2024/25 season, where his performances earned him a £25million move to AFC Bournemouth last summer.

11. Ben Gannon-Doak

The most recent name to play for both clubs, Gannon-Doak, began his career in the Celtic academy, making his debut as a late substitute in a clash with Dundee United at just 16. Snapped up by Liverpool shortly afterwards, he had his first real taste of regular football on loan to Middlesbrough in the 2024/25 season, where his performances earned him a £25million move to AFC Bournemouth last summer. | Getty Images Photo: Getty Images

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