An England youth product, Cattermole has earned a reputation as a tough-tackling midfielder due to his lengthy disciplinary record.

After making his debut for the club in January 2006, he became a regular player, and at the age of 18 years and 47 days was the youngest man to captain Middlesbrough where he made 91 appearances and scored four goals.

[4] Manager Steve McClaren later hailed his performance stating, "When we needed people to stand up and be counted, it took a 17-year-old to bring everyone together.

[10] Cattermole became Middlesbrough's youngest-ever captain aged 18 years and 47 days when he skippered the side in their 1–0 defeat away against Fulham on 7 May 2006.

[16] On 4 March, he was given a straight red card, his second of the season, for a reckless challenge on Scott Parker in the home defeat by West Ham.

[17] Despite being tied to a three-year deal,[citation needed] Cattermole's impressive season with Wigan resulted in him being a target for other clubs.

Cattermole played most of the 90 minutes in Sunderland's 3–0 away win against Chelsea, coming off in added time in the second half and was pivotal in the victory.

Following Bruce's sacking and the appointment of Martin O'Neill as his successor, it was suggested Cattermole might lose the captaincy, especially after he and Nicklas Bendtner were arrested for allegedly damaging cars in Newcastle city centre.

Cattermole and his teammates constantly pressed the Arsenal players when they had possession, forcing mistakes and with counter-attacking football, the Black Cats won 2–0.

[26] During his ban, reports suggested Cattermole could be stripped of the captaincy because of his behaviour at the Tyne-Wear Derby match but O'Neill denied the claims.

[29] The start of the 2013–14 season saw Cattermole replaced as captain by John O'Shea and his number 6 shirt handed to new signing Cabral.

[35] After missing most of the 2016–17 season through injury, Cattermole returned to the first team late in the campaign and earned praise from Sunderland fans for his performance against Arsenal at the Emirates Stadium on 16 May 2017 as the Black Cats were defeated 2–0 thanks to a brace from Alexis Sánchez.

[36][37] Cattermole suffered relegation with Sunderland as the club finished bottom of the table on just 24 points, ending their ten-year stint in the top flight.

[41][42] On 22 August 2019, Cattermole relocated to Dutch football, signing a year-long contract with Eredivisie side VVV-Venlo, joining them on a free transfer.

[43] Cattermole was released on 27 May 2020, shortly after the season was abandoned as a result of the COVID-19 pandemic, with him leaving on the grounds that his contract had expired and the club opted not to renew it.

[48] In December 2024, Cattermole joined League One side Bristol Rovers as first-team coach with a focus on the development and implementation of set-pieces.

[50] Before the first match of his caretaker reign however, it was reported that Cattermole had left the club,[51] officially confirmed following the appointment of Iñigo Calderón.