© Imago
Head-to-head record
Previous meetings: 47
Ipswich wins: 10
Draws: 11
Chelsea wins: 26
Only on 47 previous occasions have these two faced off, and just to prove how much time flies in football, between Ipswich's relegation in 2002 and their return in 2024, Chelsea had been taken over by a Russian oligarch, won numerous Premier League titles and the Champions League twice, after doing neither previously.
Despite both being well over 100 years old as footballing institutions, Chelsea and Ipswich did not cross paths at all until 1961, and the results and league positions that season would certainly surprise the modern-day fan.
A 5-2 win at Portman Road for the Tractor Boys helped them to their first and only English league title, in the same campaign that Chelsea were relegated to the Second Division.
It took the Blues just one year to return to the top flight though, and in that same season, Ipswich quickly hit rock bottom, and suffered relegation themselves, partly thanks to home and away defeats to Chelsea.
From 1963-64 onwards, Chelsea would go on a 13-game unbeaten streak against Ipswich, but they suffered another slump, falling into the second tier again in the late 1980s, where they shared the same division as the East Anglian club.
Ipswich were no match though, losing all four meetings in that brief spell, in Division Two and the much-maligned Zenith Data Systems Cup.
In the advent of the Premier League era, both clubs were a part of the newly-formed league in its first three iterations, and there was very little to separate them, with Chelsea leading two wins to one in the midst of three draws.
The turn of the millennium saw the return of Ipswich to the Premier League, and the 2000-01 will go down in history for them, qualifying for Europe as a newly-promoted club, even if they did lose 4-1 at Stamford Bridge that season.
Unfortunately, George Burley's men plummeted down the standings in similar fashion to the early-60s league winners, and were relegated the next season, once again only managing to take one point off Chelsea in their two meetings that season.
It took Ipswich over two decades to get back to the top table, but when they did in 2024-25, they marked it with a famous win over Chelsea at Portman Road, with the Blues being the first team to lose there that season at the end of December, going down 2-0.
In the two-decade spell outside the top flight, Ipswich still faced Chelsea twice, both in the FA Cup, but were unable to topple one of the heavyweights of English football, being one of the opponents the Blues beat on their way to winning the trophy in 2009.
Two years later, they were paired together again, and Chelsea showed no mercy, annihilating the Tractor Boys 7-0 at the Bridge in the third round, with Frank Lampard and Daniel Sturridge both netting twice.
However, undoubtedly the most notable cup meeting between the two came in the quarter-finals of the League Cup in 1997-98, where Chelsea needed penalties to beat Ipswich, going on to beat Middlesbrough in the final - their first trophy before many years of unprecedented success, which all may never have happened had they not won on spot kicks at Portman Road.
Last 20 meetings
Apr 13, 2025: Chelsea 2-2 Ipswich (Premier League)
Dec 30, 2024: Ipswich 2-0 Chelsea (Premier League)
Jan 09, 2011: Chelsea 7-0 Ipswich (FA Cup Third Round)
Jan 24, 2009: Chelsea 3-1 Ipswich (FA Cup Fourth Round)
Apr 01, 2002: Ipswich 0-0 Chelsea (Premier League)
Nov 04, 2001: Chelsea 2-1 Ipswich (Premier League)
Jan 20, 2001: Chelsea 4-1 Ipswich (Premier League)
Dec 26, 2000: Ipswich 2-2 Chelsea (Premier League)
Jan 07, 1998: Ipswich 2-2p Chelsea (League Cup Quarter-Final)
Jan 21, 1995: Ipswich 2-2 Chelsea (Premier League)
Oct 23, 1994: Chelsea 2-0 Ipswich (Premier League)
Dec 11, 1993: Chelsea 1-1 Ipswich (Premier League)
Aug 21, 1993: Ipswich 1-0 Chelsea (Premier League)
Apr 06, 1993: Ipswich 1-1 Chelsea (Premier League)
Oct 17, 1992: Chelsea 2-1 Ipswich (Premier League)
Nov 26, 1991: Chelsea p2-2 Ipswich (Zenith Data Systems Cup)
Jan 23, 1990: Ipswich 2-3 Chelsea (Zenith Data Systems Cup)
Mar 28, 1989: Ipswich 0-1 Chelsea (Division Two)
Dec 26, 1988: Chelsea 3-0 Ipswich (Division Two)
Apr 05, 1986: Chelsea 1-1 Ipswich (Division One)
Last 10 Premier League meetings
Apr 13, 2025: Chelsea 2-2 Ipswich
Dec 30, 2024: Ipswich 2-0 Chelsea
Apr 01, 2002: Ipswich 0-0 Chelsea
Nov 04, 2001: Chelsea 2-1 Ipswich
Jan 20, 2001: Chelsea 4-1 Ipswich
Dec 26, 2000: Ipswich 2-2 Chelsea
Jan 21, 1995: Ipswich 2-2 Chelsea
Oct 23, 1994: Chelsea 2-0 Ipswich
Dec 11, 1993: Chelsea 1-1 Ipswich
Aug 21, 1993: Ipswich 1-0 Chelsea
Apr 06, 1993: Ipswich 1-1 Chelsea
Andrew Delaney
