*1990*
- In April, Lightfoot tours Atlantic Canada for the first time in 7 years, playing several cities he hadn't played in over 20 years.
- Bob Dylan's Ring Them Bells is being performed for the first time in concerts in 1990.
- Lightfoot donates $2,500 to help build a hockey arena in Superior, Wisconsin.
- Lightfoot is awarded the William Harold Moon award for his contribution to the Canadian music industry.
- Facial Hair Tracker. For the first extended period since 1971, Lightfoot goes completely clean shaven.

*1991*
- More new songs are being played live this year.  Fading Away, Only Love Would Know and Wild Strawberries are some of the first.
- Folk revival icon and Lightfoot influence, Bob Gibson attends Lightfoot's Chicago show in July and is acknowledged from the stage by Lightfoot.
- In August Lightfoot performs Oh Canada at the Toronto Argonauts home game at Skydome as a favour to team co-owner John Candy.
- Lightfoot plays Drink Yer Glasses Empty on CBC radio's Morningside during an interview.  The lyrics here are quite different than on the final  recorded version.

*1992*
- Lightfoot is named honorary captain of the Toronto Maple Leafs for the new season and drops the ceremonial opening puck at their first home game.
- Lightfoot's UA albums are finally released on CD, a 3 CD package titled The Original Lightfoot.

*1993*

- In April, Waiting For You is released.
- In May, Lightfoot plays in Charleston, SC as part the Mountain Stage Live radio series.
- In November, Lightfoot plays the Skydome in Toronto on a bill with Simon and Garfunkel.
- Lightfoot wins 12 SOCAN career airplay awards (Anything For Love, Carefree Highway, Cotton Jenny, Daylight Katy, The Circle Is Small, Early Morning Rain, If You Could Read My Mind, Rainy Day People, That Same Old Obsession, Sundown, The Wreck Of The Edmund Fitzgerald), signifying that they have been played over 100,000 times each on Canadian radio.

*1994*
- Late in the year Lightfoot records demos for 6 new songs for a new album which is still over two years away.
- In June, Massey Hall turned 100 years old and Lightfoot is among the performers there to celebrate the occasion.
- In July, CBC draws fire for the unauthorized use of a sound clip from The Wreck Of The Edmund Fitzgerald during a news magazine piece about the ship.

*1995*
- At the Mariposa folk festival in Toronto, a special tribute night is given in Lightfoot's honor and Lightfoot surprises everyone by showing up and doing Knotty Pine and I'll Tag Along.
- In the fall, Lightfoot takes a tour of Daniel Lanois' Grant Avenue studio in Hamilton, and considers it as the location to record his new album.
- In November, on the 20th anniversary of the Edmund Fitzgerald's sinking, Lightfoot is in Whitefish Point, MI to ring the ship's bell at a ceremony attended by many family members of the Fitzgerald crew.

*1996*
- In February, Lightfoot begins recording sessions for a new album at the Grant Avenue studio in Hamilton near Toronto.
- Lightfoot flies to Los Angeles to tape a couple of songs for the TV special, Global Dreams, which airs in March.
- In March, Lightfoot performs If You Could Read My Mind at the 25th annual Juno Awards.
- Lightfoot undertakes a spring tour beginning in Chicago in March and winding up in Orillia in May.
- After the spring tour, recording sessions resume in Hamilton and they continue off and on until touring resumes in November.
- At Ontario concerts in November, Lightfoot has incorporated 6 new songs into his setlists.  Titles include A Painter Passing Through, On Yonge Street, Boathouse and Uncle Toad Said.
- In December, more recording is continued in Hamilton.

*1997*
- Lightfoot continues recording work on A Painter Passing Through during the early months of '97.
- Touring begins in May and continues through June in the western US and moves east in July.
- Another new song, Ring Neck Loon is being played during the spring/summer tour.
- Recording work on the new album is continued during breaks in the tour.
- Santa Fe concert on June 26 is cancelled due to heavy rains which flooded the amphitheatre.
- Lightfoot undertakes a two week midwest tour in September.
- The concert hall at the Orillia Opera House is named the Gordon Lightfoot Auditorium at a ceremony prior to a benefit concert Lightfoot gives there in October.
- Pee Wee Charles sits in on pedal steel at the Orillia concert to substitute for Mike Heffernan who was unable to perform due to illness.
- In November, Lightfoot is presented with the Governor General's Arts Award at a presentation in Ottawa. Ian Tyson is on hand to perform a few Lightfoot songs at the reception following the ceremonies.
- On New Year's Eve, Lightfoot appears on Pamela Wallin Live to discuss his resolutions for the upcoming year.

*1998*

- Lightfoot launches his 1998 tour with two shows in Windsor, ON in late April.
- Lightfoot makes a one hour TV appearance in conversation with Peter Gzowski on May 1 on CBC.
- Lightfoot's new album, "A Painter Passing Through" is released on May 5 in Canada and May 12 in the US.
- Lightfoot signs autographs for an hour at Sam the Record Man in downtown Toronto on May 5, the day the new album is released.
- Lightfoot is among the inaugural members inducted into the new Canadian Walk Of Fame in Toronto.  Out on tour, he is unable to attend the ceremony.  In June, Lightfoot performs on the Mountain Stage Live radio show from Charleston, WV as part of his summer concert tour. 
- In July, Lightfoot tapes another radio show, this time in Boulder, CO, featuring an interview segment mixed with performances. 
- In the late summer and fall, Lightfoot is working with Rhino records on track selection for a 4 CD box set due in 1999, including previously unreleased material.
- In October, Lightfoot is present for the launch of MuchMoreMusic at City-TV in Toronto.
- In November, Lightfoot, along with Christopher Plummer, is present for a ceremony officially laying his star on the Canadian Walk Of Fame.
- Also in November, Lightfoot attends the SOCAN awards in Toronto.
- In December, Lightfoot puts his Rosedale mansion, his home since 1975, for sale.
- Facial Hair Tracker. Late in 1998 Lightfoot appears again with his moustache.