Abramovich's Chelsea

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Season Manager Domestic Continental
League FA Cup EFL Cup Champions League Europa League Europa Conference
2004–05   José Mourinho 1st Round of 16
0-1 Newcastle
Winners
3-2 v. Liverpool
Semi-final
0-1 (agg) v. Liverpool
n/a
2005–06 1st Semi-final
1-2 v. Liverpool
Round of 32
1-1 v. Charlton
Round of 16
2-3 (agg) v. Barcelona
n/a
2006–07 2nd Winners
1-0 v. Man United
Winners
2-1 v. Arsenal
Semi-final
1-1 (agg) v. Liverpool
n/a
2007–08   Avram Grant 2nd Quarter-final
0-1 v. Barnsley
Runners Up
1-2 v. Tottenham
Runners Up
1-1 v. Man United
n/a
2008–09   Luiz Felipe Scolari
  Gus Hiddink
3rd Winners
2-1 v. Everton
Round of 16
1-1 v. Burnley
Semi-final
1-1 (agg) v. Barcelona
n/a
2009–10   Carlo Ancelotti 1st Winners
1-0 v. Portsmouth
Quarter-final
3-3 v. Blackburn
Round of 16
1-3 (agg) v. Inter
n/a
2010-11 2nd Round of 32
1-1 v. Everton
Round of 32
3-4 v. Newcastle
Quarter-final
1-3 (agg) v. Man United
n/a
2011–12   André Villas-Boas
  Roberto Di Matteo
6th Winners
2-1 v. Liverpool
Quarter-final
0-2 v. Liverpool
Winners
1-1 v. Bayern
n/a
2012–13   Roberto Di Matteo
  Rafael Benítez
3rd Semi-final
1-2 v. Man City
Semi-final
0-2 v. Swansea
Group Stage
3rd
Winners
2-1 v. Benfica
2013–14   José Mourinho 3rd Round of 16
0-2 v. Man City
Quarter-final
1-2 v. Sunderland
Semi-final
1-3 (agg) v. Atlético
n/a
2014–15 1st Round of 32
2-4 v. Bradford
Winners
2-0 v. Tottenham
Round of 16
3-3 (agg) v. PSG
n/a
2015–16   José Mourinho
  Gus Hiddink
10th Quarter-final
0-2 v. Everton
Round of 16
1-1 v. Stoke City
Round of 16
2-4 (agg) v. PSG
n/a
2016–17   Antonio Conte 1st Runners Up
1-2 v. Arsenal
Round of 16
1-2 v. West Ham
DNQ
2017–18 5th Winners
1-0 v. Man United
Semi-final
1-2 v. Arsenal
Round of 16
1-4 (agg) v. Barcelona
n/a
2018–19   Maurizio Sarri 3rd Round of 16
0-2 v. Man United
Runners Up
0-1 v. Man City
DNQ Winners
4-1 v. Arsenal
2019–20   Frank Lampard 4th Runners Up
1-2 v. Arsenal
Round of 16
1-2 v. Man United
Round of 16
1-7 (agg) v. Bayern
n/a
2020–21   Frank Lampard
  Thomas Tuchel
4th Runners Up
0-1 v. Leicester
Round of 16
1-1 v. Tottenham
Winners
1-0 v. Man City
n/a
2021–22   Thomas Tuchel 3rd Runners Up
0-0 v. Liverpool
Runners Up
0-0 v. Liverpool
Quarter-final
4-5 (agg) v. Real Madrid
n/a
2022-23   Thomas Tuchel
  Graham Potter
12th Round of 64
0-4 v. Man City
Round of 32
0-2 v. Man City
Quarter-final
0-4 (agg) v. Real Madrid
n/a
2023-24   Mauricio Pochettino 12th Semi-final Runners Up
0-1 v. Liverpool
DNQ

Levy's Tottenham Hotspur

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Season Manager Domestic Continental
League FA Cup EFL Cup Champions League Europa League Europa Conference
2001–02   Glenn Hoddle 9th Quarter-final
0-4 v. Chelsea
Runners Up
1-2 v. Blackburn
DNQ
2002–03 10th Round of 64
0-4 v. Southampton
Round of 32
1-2 v. Burnley
DNQ
2003–04   Glenn Hoddle
  David Pleat
14th Round of 32
3-4 v. Man City (Replay)
Quarter-final
1-1 v. Middlesborough
DNQ
2004–05   Jacques Santini
  Martin Jol
9th Quarter-final
0-1 v. Newcastle
Quarter-final
1-1 v. Liverpool
DNQ
2005–06   Martin Jol 5th Round of 64
2-3 v. Leicester
Second Round
0-1 v. Grimsby
DNQ
2006–07 5th Quarter-final
1-2 v. Chelsea
Semi-final
1-3 v. Arsenal
DNQ Quarter-final
3-4 v. Sevilla
2007–08   Martin Jol
  Juande Ramos
11th Round of 32
1-3 v. Man United
Winners
1-2 v. Chelsea
DNQ Round of 16
1-1 v. PSV
2008–09   Juande Ramos
  Harry Redknapp
8th Round of 32
1-2 v. Man United
Runners-Up
0-0 v. Man United
DNQ Round of 32
1-3 v. Shakhtar
2009–10   Harry Redknapp 4th Semi-final
0-2. v Portsmouth
Quarter-final
0-2 v. Man United
DNQ
2010–11 5th Round of 32
0-4 v. Fulham
Round of 32
1-4 v. Arsenal
Quarter-final
0-5 v. Real Madrid
n/a
2011–12 4th Semi-final
1-5 v. Chelsea
Round of 32
0-0 v. Stoke City
DNQ Group Stage
3rd
2012–13   André Villas-Boas 5th Round of 32
1-2 v. Leeds
Round of 16
1-2 v. Norwich
Quarter-final
4-4 v. Basel
n/a
2013–14   André Villas-Boas
  Tim Sherwood
6th Round of 64
0-2 v. Arsenal
Quarter-final
1-2 v. West Ham
DNQ Round of 16
3-5 v. Benfica
2014–15   Mauricio Pochettino 5th Round of 32
1-2 v. Leicester
Runners Up
0-2 v. Chelsea
DNQ Round of 32
1-3 v. Fiorentina
2015–16 3rd Round of 16
0-1 v. Crystal Palace
Round of 32
1-2 v. Arsenal
DNQ Round of 16
1-5 v. Dortmund
2016–17 2nd Semi-final
2-4 v. Chelsea
Round of 16
1-2 v. Liverpool
Group Stage
3rd
Round of 32
2-3 v. Gent
2017–18 3rd Semi-final
1-2 v. Man United
Round of 16
2-3 v. West Ham
Round of 16
3-4 v. Juventus
n/a
2018–19 4th Round of 32
0-2 v. Crystal Palace
Semi-final
2-2 v. Chelsea
Runners Up
0-2 v. Liverpool
n/a
2019–20   Mauricio Pochettino
  José Mourinho
6th Round of 16
1-1 v. Norwich
Round of 32
0-0 v. Colchester
Round of 16
0-4 v. Leipzig
n/a
2020–21   José Mourinho
  Ryan Mason
7th Round of 16
4-5 v. Everton
Runners Up
0-1 v. Man City
DNQ Round of 16
2-3 v. Zagreb
2021–22   Nuno Espírito Santo
  Antonio Conte
4th Round of 16
0-1 v. Middlesborough
Semi-final
0-3 v. Chelsea
DNQ Group Stage
3rd
2022–23   Antonio Conte 4th Round of 16
0-1 v. Sheffield Utd
Round of 32
0-2 v. Notts Forest
Round of 16
0-1 v. Milan
n/a