Yes this is the first Round.
Chris Jericho
Chris Jericho won the IC title on December 12th 1999 at Armageddon from Chyna, A double pinfall with Chyna on the December 30th 1999 Smackdown made them Co-Champions and the belt was declared vacant even though both cleared to share the title. Jericho defeated Chyna and Hardcore Holly on January 23rd 2000 at The Royal Rumble making him a 2 time Champion. He lost the title to Kurt Angle on February 27th 2000 to Kurt Angle at No Way Out. Jericho won his 3rd IC title on the May 4th 2000 Smackdown from Chris Benoit. He lost the belt back to Benoit on May 8th 2000 on Raw. He won his 4th title from Benoit on January 21st 2001 at The Royal Rumble in a Ladder Match. He lost the title to Triple H on the April 5th 2001 Smackdown. He won his 5th title on September 16th 2002 on Raw from Rob Van Dam. He lost the title to Kane on the September 30th 2002 Raw. He won his 6th title on the October 27th 2003 Raw from Rob Van Dam. He lost the belt to RVD in a Steel Cage Match the same night. He won his 7th title on September 12th 2004 at Unforgiven by defeating Christian in a Ladder Match. He lost the belt to Shelton Benjamin on October 19th 2004 at Taboo Tuesday. He won his 8th title on the March 10th 2008 Raw from Jeff Hardy. He lost the belt to Kofi Kingston on June 29th 2008 at Night Of Champions. He won his 9th IC title from Rey Mysterio at Extreme Rules on June 7th 2009 in a No Holds Barred Match. He lost the belt back to Mysterio at The Bash on June 28th 2009 in a Mask vs Title Match
vs
Randy Savage
Randy "Macho Man" Savage won the IC title on Feburary 8th 1986 in Boston from Tito Santana, He lost the belt to Ricky Steamboat at Wrestlemania III on March 29th 1987.
Chris Jericho
Chris Jericho won the IC title on December 12th 1999 at Armageddon from Chyna, A double pinfall with Chyna on the December 30th 1999 Smackdown made them Co-Champions and the belt was declared vacant even though both cleared to share the title. Jericho defeated Chyna and Hardcore Holly on January 23rd 2000 at The Royal Rumble making him a 2 time Champion. He lost the title to Kurt Angle on February 27th 2000 to Kurt Angle at No Way Out. Jericho won his 3rd IC title on the May 4th 2000 Smackdown from Chris Benoit. He lost the belt back to Benoit on May 8th 2000 on Raw. He won his 4th title from Benoit on January 21st 2001 at The Royal Rumble in a Ladder Match. He lost the title to Triple H on the April 5th 2001 Smackdown. He won his 5th title on September 16th 2002 on Raw from Rob Van Dam. He lost the title to Kane on the September 30th 2002 Raw. He won his 6th title on the October 27th 2003 Raw from Rob Van Dam. He lost the belt to RVD in a Steel Cage Match the same night. He won his 7th title on September 12th 2004 at Unforgiven by defeating Christian in a Ladder Match. He lost the belt to Shelton Benjamin on October 19th 2004 at Taboo Tuesday. He won his 8th title on the March 10th 2008 Raw from Jeff Hardy. He lost the belt to Kofi Kingston on June 29th 2008 at Night Of Champions. He won his 9th IC title from Rey Mysterio at Extreme Rules on June 7th 2009 in a No Holds Barred Match. He lost the belt back to Mysterio at The Bash on June 28th 2009 in a Mask vs Title Match
vs
Randy Savage
Randy "Macho Man" Savage won the IC title on Feburary 8th 1986 in Boston from Tito Santana, He lost the belt to Ricky Steamboat at Wrestlemania III on March 29th 1987.