Chelsea 4-2 Barcelona (5-4 aggregate) – March 8, 2005
To this day, it remains one of the most treasured European nights at Stamford Bridge.
An electrifying start saw Chelsea race into a three-goal lead and take command of the tie within 19 minutes, but the magical Ronaldinho turned it back in Barcelona's favour before the interval – converting a fantastic outside-of-the-boot finish from the edge of the area.
The match remained level until the 76th minute, when Terry rose to steer a corner from Damien Duff across the face of goal and inside the far post of Victor Valdes' goal, wheeling away in euphoria.
Captain Terry then helped Chelsea stave off a late Barca onslaught and book their place in the UEFA Champions League quarter-finals.
In his first season after being appointed captain by Jose Mourinho, it was a performance that epitomised the determination and strength of character that would come to define his many years as skipper.
Although they fell short in Europe, Chelsea claimed their first top-flight title in 50 years at the end of the season.
Chelsea 3-0 Manchester United – April 29, 2006
All that was needed was one point. A draw against their closest rivals in the race for the Premier League title and Chelsea would be champions of England once more.
Their push had once again been built on the foundation of an exceptional defence.
Ahead of the clash at Stamford Bridge, the Blues had conceded just 20 goals in their 35 top-flight matches, and the backline shone once again on a crucial day in the capital.
After William Gallas had given Chelsea the lead, Terry went down injured after a battle with Louis Saha and Wayne Rooney, caught by the latter having won a stretching challenge.
He received treatment on a bleeding foot, but the centre-back played on.
Terry helped underpin a formidable display as Chelsea surged to a comprehensive win courtesy of second-half strikes from Joe Cole and Ricardo Carvalho.
It completed back-to-back title triumphs, setting new standards at Stamford Bridge for the foreseeable future.
Chelsea 1-0 Manchester United – November 8, 2009
Terry produced one of his finest all-round displays in this crucial victory in their double-winning campaign.
The Blues had been second best to the reigning champions at Stamford Bridge, but remained resolute at the back to restrict Alex Ferguson's side to relatively few chances, with Terry a pivotal figure.
Not content with his defensive mettle, Terry promptly made the difference at the other end of the pitch, rising highest to head in Frank Lampard's free-kick with 14 minutes of normal time remaining.
Chelsea held firm in the closing stages to move points clear of United in the table and take a big step towards their first title since 2006.
They would go on to win the reverse fixture at Old Trafford en route to a league and FA Cup double.
Chelsea 4-1 Napoli (aet, 5-4 aggregate) – March 14, 2012
A 3-1 first-leg defeat in the Champions League last 16 at the San Paolo brought an end to Andre Villas-Boas' time as manager after less than 10 months in charge.
Roberto Di Matteo took charge for the remainder of the season and he oversaw a huge result that catapulted Chelsea into the last eight.
Terry added to a first-half strike from Didier Drogba after the interval, looping a trademark header into the far corner.
Gokhan Inler threw a spanner in the works, but Lampard returned fire from the penalty spot to force extra time, where Branislav Ivanovic secured a memorable triumph by drilling the ball into the roof of the net.
It sparked a run to the final, where Chelsea claimed their first European Cup win.
Their displays were marked by stoic defensive tactics, underpinned by the captain until the final, which he missed through suspension.
After the pain in Moscow four years prior, Chelsea had the biggest trophy in European club football in their grasp.
Arsenal 0-0 Chelsea - April 26, 2015
Terry found game time limited during Rafael Benitez's spell as interim manager, but Mourinho showed faith in the centre-back by restoring him to an integral position after his return.
Chelsea finished third in his first season back at the helm, but, after some key additions in Cesc Fabregas and Diego Costa, the Blues regained the title the season after.
A key moment along the way came at the Emirates Stadium, where Terry marshalled a solid defensive display.
Chelsea kept Arsenal off the scoresheet to take a huge step towards the title, with the captain dominating the majority of crosses they sent into the box.
A crucial challenge on Mesut Ozil in the second half proved his ability to read the game made up for any loss in pace.
It was a display that garnered special praise from Mourinho, who said: "I told John Terry in the dressing room that he has produced some fantastic performances with me, but this was his best."