Group A
17/09/2008 01:00 D.C. United - Deportivo Saprissa 0:2 (0:1)
18/09/2008 03:00 CD Marathón - Cruz Azul 2:0 (1:0)
24/09/2008 03:00 Cruz Azul - Deportivo Saprissa 4:0 (1:0)
25/09/2008 03:00 CD Marathón - D.C. United 2:0 (0:0)
01/10/2008 03:00 Deportivo Saprissa - CD Marathón 2:1 (0:0)
02/10/2008 01:00 D.C. United - Cruz Azul 0:1 (0:0)
08/10/2008 01:00 Cruz Azul - CD Marathón 1:1 (1:0)
10/10/2008 03:00 Deportivo Saprissa - D.C. United 2:2 (0:1)
22/10/2008 03:00 Cruz Azul - D.C. United 2:0 (1:0)
30/10/2008 00:00 D.C. United - CD Marathón 2:4 (1:1)
02:00 Deportivo Saprissa - Cruz Azul 1:0 (0:0)
06/11/2008 01:00 CD Marathón - Deportivo Saprissa 2:0 (1:0)
Group B
17/09/2008 03:00 San Francisco FC - Pumas UNAM 1:1 (1:1)
24/09/2008 01:00 San Francisco FC - Houston Dynamo 0:0 (0:0)
25/09/2008 03:00 Pumas UNAM - Luis Angel Firpo 3:0 (3:0)
01/10/2008 03:00 Pumas UNAM - Houston Dynamo 4:4 (4:3)
02/10/2008 03:00 Luis Angel Firpo - San Francisco FC 1:0 (0:0)
08/10/2008 03:00 Houston Dynamo - San Francisco FC 2:1 (1:0)
10/10/2008 03:00 Luis Angel Firpo - Pumas UNAM 1:1 (0:0)
23/10/2008 01:00 San Francisco FC - Luis Angel Firpo 2:3
03:00 Houston Dynamo - Pumas UNAM 1:3 (1:2)
29/10/2008 02:00 Luis Angel Firpo - Houston Dynamo 1:1
30/10/2008 00:00 Pumas UNAM - San Francisco FC 6:0 (2:0)
27/11/2008 01:00 Houston Dynamo - Luis Angel Firpo 1:0
Group C
18/09/2008 01:00 Impact de Montréal - Joe Public FC 2:0
19/09/2008 03:00 CF Atlante - CD Olimpia 1:0
25/09/2008 01:00 Joe Public FC - CD Olimpia 1:3
01:00 Impact de Montréal - CF Atlante 0:0
02/10/2008 03:00 CD Olimpia - Impact de Montréal 1:2
03/10/2008 03:00 CF Atlante - Joe Public FC 0:1
09/10/2008 01:00 Joe Public FC - Impact de Montréal 1:4
03:00 CD Olimpia - CF Atlante 1:1
22/10/2008 01:00 Joe Public FC - CF Atlante 0:2
01:00 Impact de Montréal - CD Olimpia 1:1
29/10/2008 00:00 CD Olimpia - Joe Public FC 4:0
02:00 CF Atlante - Impact de Montréal 2:1
Group D
17/09/2008 01:00 Puerto Rico Islanders - Tauro FC 2:1
18/09/2008 01:00 Santos Laguna - CSD Municipal 3:2
24/09/2008 01:00 Puerto Rico Islanders - Santos Laguna 3:1
26/09/2008 01:00 Tauro FC - CSD Municipal 2:1
02/10/2008 03:00 CSD Municipal - Puerto Rico Islanders 2:2
03/10/2008 01:00 Tauro FC - Santos Laguna 2:0
09/10/2008 01:00 Santos Laguna - Puerto Rico Islanders 3:0
03:00 CSD Municipal - Tauro FC 2:2
23/10/2008 01:00 Santos Laguna - Tauro FC 3:0
24/10/2008 01:00 Puerto Rico Islanders - CSD Municipal 0:1
30/10/2008 00:00 Tauro FC - Puerto Rico Islanders 2:2
31/10/2008 02:00 CSD Municipal - Santos Laguna 4:4
Quarter-finals
25/02/2009 03:00 Houston Dynamo - CF Atlante 1:1 (1:0)
26/02/2009 01:00 Impact de Montréal - Santos Laguna 2:0 (1:0)
03:00 Cruz Azul - Pumas UNAM 1:0 (1:0)
27/02/2009 01:00 Puerto Rico Islanders - CD Marathón 2:1 (0:1)
04/03/2009 03:00 CF Atlante - Houston Dynamo 3:0 (2:0)
05/03/2009 01:00 CD Marathón - Puerto Rico Islanders 0:1 (0:0)
03:00 Pumas UNAM - Cruz Azul 0:1 (0:0)
06/03/2009 03:00 Santos Laguna - Impact de Montréal 5:2 (1:2)
Semi-finals
18/03/2009 00:00 Puerto Rico Islanders - Cruz Azul 2:0 (2:0)
19/03/2009 02:00 Santos Laguna - CF Atlante 2:1 (1:1)
08/04/2009 03:00 Cruz Azul - Puerto Rico Islanders 4:2 (1:0, 2:0, 3:1) pso
09/04/2009 03:00 CF Atlante - Santos Laguna 3:1 (1:0)
Final
23/04/2009 03:00 Cruz Azul - CF Atlante 0:2 (0:2)
13/05/2009 03:00 CF Atlante - Cruz Azul 0:0 (0:0)