This might be of interest to some readers. I have compiled as best I can the Toronto top ten lists from 1929 to 2014.

It is very possible that I have missed some candidates, or got the completion year or height wrong (in fact I know that some heights are almost certainly wrong, since I was forced to estimate several early building heights), but it should give a good idea of the top 10 buildings for each of the listed years (the years not listed would be identical to the last listed year before it). Bolded entries are buildings that were completed that year -- for years in the future I used the SSP completion date.

Toronto skyline from 1968

The TD Bank Tower, number one when completed in 1967, will soon be the 10th tallest.

1929

1 124m Royal York Hotel (1929, 28 floors)

2 103.6m Toronto City Hall (1899, 7 floors)

3 93m St. James Cathedral (1874)

4 ~88m Toronto Star Building (1929, 22 floors)

5 ~84m Royal Bank Building = Optima Business Centre (1915, 21 floors)

5 ~84m Victoria Tower (1927, 21 floors)

5 ~84m Sterling Tower (1929, 21 floors)

8 79m St. Michael's Cathedral (1867)

9 ~72m King Edward Hotel (1903, 18 floors)

10 70m Canada Building (1928, 14 floors)

1930

1 124m Royal York Hotel (1929, 28 floors)

2 103.6m Toronto City Hall (1899, 7 floors)

3 93m St. James Cathedral (1874)

4 ~88m Toronto Star Building (1929, 22 floors)

5 ~84m Royal Bank Building = Optima Business Centre (1915, 21 floors)

5 ~84m Victoria Tower (1927, 21 floors)

5 ~84m Sterling Tower (1929, 21 floors)

8 79m St. Michael's Cathedral (1867)

9 77m Canada Permanent Trust Building (1930, 18 floors)

10 ~72m King Edward Hotel (1903, 18 floors) 

1931

1 145.1m Commerce Court North (1931, 34 floors)

2 124m Royal York Hotel (1929, 28 floors)

3 103.6m Toronto City Hall (1899, 7 floors)

4 93m St. James Cathedral (1874)

5 ~88m Toronto Star Building (1929, 22 floors)

6 87m Canada Life Building (1931, 15 floors)

7 ~84m Royal Bank Building = Optima Business Centre (1915, 21 floors)

7 ~84m Victoria Tower (1927, 21 floors)

7 ~84m Sterling Tower (1929, 21 floors) 1

0 79m St. Michael's Cathedral (1867)

1951

1 145.1m Commerce Court North (1931, 34 floors)

2 124m Royal York Hotel (1929, 28 floors)

3 115m Bank of Nova Scotia Building (1951, 27 floors)

4 103.6m Toronto City Hall (1899, 7 floors)

5 93m St. James Cathedral (1874)

6 ~88m Toronto Star Building (1929, 22 floors)

7 87m Canada Life Building (1931, 15 floors)

8 ~84m Royal Bank Building = Optima Business Centre (1915, 21 floors)

8 ~84m Victoria Tower (1927, 21 floors)

8 ~84m Sterling Tower (1929, 21 floors)

1957

1 145.1m Commerce Court North (1931, 34 floors)

2 124m Royal York Hotel (1929, 28 floors)

3 115m Bank of Nova Scotia Building (1951, 27 floors)

4 103.6m Toronto City Hall (1899, 7 floors)

5 93m St. James Cathedral (1874)

6 ~88m Toronto Star Building (1929, 22 floors)

7 87m Canada Life Building (1931, 15 floors)

8 ~84m Royal Bank Building = Optima Business Centre (1915, 21 floors)

8 ~84m Victoria Tower (1927, 21 floors)

8 ~84m Sterling Tower (1929, 21 floors) 8 ~84m Imperial Oil Building (1957, 21 floors)

1962

1 145.1m Commerce Court North (1931, 34 floors)

2 124m Royal York Hotel (1929, 28 floors)

3 115m Bank of Nova Scotia Building (1951, 27 floors)

4 103.6m Toronto City Hall (1899, 7 floors)

5 93m St. James Cathedral (1874)

6 ~90m Canada Square North (1962, 17 floors)

7 ~88m Toronto Star Building (1929, 22 floors)

8 87m Canada Life Building (1931, 15 floors)

9 ~84m Royal Bank Building = Optima Business Centre (1915, 21 floors)

9 ~84m Victoria Tower (1927, 21 floors)

9 ~84m Sterling Tower (1929, 21 floors)

9 ~84m Imperial Oil Building (1957, 21 floors)

1965

1 145.1m Commerce Court North (1931, 34 floors)

2 124m Royal York Hotel (1929, 28 floors)

3 115m Bank of Nova Scotia Building (1951, 27 floors)

4 103.6m Toronto City Hall (1899, 7 floors)

5 99.7m New City Hall (1965, 27 floors)

6 93m St. James Cathedral (1874)

7 ~90m Canada Square North (1962, 17 floors)

8 ~88m Toronto Star Building (1929, 22 floors)

9 87m Canada Life Building (1931, 15 floors)

10 ~84m Royal Bank Building = Optima Business Centre (1915, 21 floors)

10 ~84m Victoria Tower (1927, 21 floors)

10 ~84m Sterling Tower (1929, 21 floors)

10 ~84m Imperial Oil Building (1957, 21 floors)

10 ~84m 2 St. Clair West (1965, 21 floors)

1966

1 145.1m Commerce Court North (1931, 34 floors)

2 124m Royal York Hotel (1929, 28 floors)

3 115m Bank of Nova Scotia Building (1951, 27 floors) 4 104m Richmond-Adelaide Centre I (1966, 26 floors)

5 103.6m Toronto City Hall (1899, 7 floors)

6 99.7m New City Hall (1965, 27 floors)

7 93m St. James Cathedral (1874)

8 ~90m Canada Square North (1962, 17 floors)

9 ~88m Toronto Star Building (1929, 22 floors)

10 87m Canada Life Building (1931, 15 floors)

1967

1 222.9m TD Tower (1967, 56 floors)

2 145.1m Commerce Court North (1931, 34 floors)

3 124m Royal York Hotel (1929, 28 floors)

4 115m Bank of Nova Scotia Building (1951, 27 floors)

5 104m Richmond-Adelaide Centre I (1966, 26 floors)

5 104m The Sutton Place Hotel (1967, 32 floors)

7 103.6m Toronto City Hall (1899, 7 floors)

8 99.7m New City Hall (1965, 27 floors)

9 93m St. James Cathedral (1874)

10 ~90m Canada Square North (1962, 17 floors)

10 ~90m Forester's House (1967, 23 floors)

1968

1 222.9m TD Tower (1967, 56 floors)

2 145.1m Commerce Court North (1931, 34 floors)

3 139.9m Simpson Tower (1968, 32 floors)

4 124m Royal York Hotel (1929, 28 floors)

5 115m Bank of Nova Scotia Building (1951, 27 floors)

6 104m Richmond-Adelaide Centre I (1966, 26 floors)

7 104m The Sutton Place Hotel (1967, 32 floors)

8 103.6m Toronto City Hall (1899, 7 floors)

9 99.7m New City Hall (1965, 27 floors)

10 93m St. James Cathedral (1874)

1969

1 222.9m TD Tower (1967, 56 floors)

2 183m Royal Trust Tower (1969, 46 floors)

3 145.1m Commerce Court North (1931, 34 floors)

4 139.9m Simpson Tower (1968, 32 floors)

5 124m Royal York Hotel (1929, 28 floors)

6 115m Bank of Nova Scotia Building (1951, 27 floors)

7 106m Mowat Block (1969, 24 floors)

8 104m Richmond-Adelaide Centre I (1966, 26 floors)

8 104m The Sutton Place Hotel (1967, 32 floors)

10 103.6m Toronto City Hall (1899, 7 floors)

1970

1 222.9m TD Tower (1967, 56 floors)

2 183m Royal Trust Tower (1969, 46 floors)

3 145.1m Commerce Court North (1931, 34 floors)

4 139.9m Simpson Tower (1968, 32 floors)

5 129m Leaside Towers West (1970, 44 floors)

5 129m Leaside Towers West (1970, 44 floors)

7 124m Royal York Hotel (1929, 28 floors)

8 115m Bank of Nova Scotia Building (1951, 27 floors)

9 106m Mowat Block (1969, 24 floors)

10 104m Richmond-Adelaide Centre I (1966, 26 floors)

10 104m The Sutton Place Hotel (1967, 32 floors)

1971

1 222.9m TD Tower (1967, 56 floors)

2 183m Royal Trust Tower (1969, 46 floors)

3 145.1m Commerce Court North (1931, 34 floors)

4 139.9m Simpson Tower (1968, 32 floors)

5 129m Leaside Towers West (1970, 44 floors)

5 129m Leaside Towers West (1970, 44 floors)

7 124m Royal York Hotel (1929, 28 floors)

8 115m Bank of Nova Scotia Building (1951, 27 floors)

9 112m Bank of Zurich Building (1971, 24 floors)

10 106m Mowat Block (1969, 24 floors)

1972

1 239m Commerce Court West (1972, 57 floors)

2 222.9m TD Tower (1967, 56 floors)

3 183m Royal Trust Tower (1969, 46 floors)

4 163m 44 Charles Street West (1972, 51 floors)

5 146m 2 Bloor West (1972, 34 floors)

6 145.1m Commerce Court North (1931, 34 floors)

7 139.9m Simpson Tower (1968, 32 floors)

[b]8 135m Sheraton Centre Hotel (1972, 43 floors)[/b]

9 129m Leaside Towers West (1970, 44 floors)

9 129m Leaside Towers West (1970, 44 floors)

1973

1 239m Commerce Court West (1972, 57 floors)

2 222.9m TD Tower (1967, 56 floors)

3 183m Royal Trust Tower (1969, 46 floors)

4 163m 44 Charles Street West (1972, 51 floors)

5 146m 2 Bloor West (1972, 34 floors)

6 145.1m Commerce Court North (1931, 34 floors)

7 139.9m Simpson Tower (1968, 32 floors)

7 139.9m Hudson's Bay Centre (1973, 35 floors)

9 135m Sheraton Centre Hotel (1972, 43 floors)

10 129m Leaside Towers West (1970, 44 floors)

10 129m Leaside Towers West (1970, 44 floors)

1975

1 298m First Canadian Place (1975, 72 floors)

2 239m Commerce Court West (1972, 57 floors)

3 222.9m TD Tower (1967, 56 floors)

4 183m Royal Trust Tower (1969, 46 floors)

5 163m 44 Charles Street West (1972, 51 floors)

6 146m 2 Bloor West (1972, 34 floors)

7 145.1m Commerce Court North (1931, 34 floors)

8 139.9m Simpson Tower (1968, 32 floors

8 139.9m Hudson's Bay Centre (1973, 35 floors)

10 135m Sheraton Centre Hotel (1972, 43 floors)

1976

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 239m Commerce Court West (1972, 57 floors)

4 222.9m TD Tower (1967, 56 floors)

5 183m Royal Trust Tower (1969, 46 floors)

6 180m Royal Bank Plaza South (1976, 41 floors)

7 163m 44 Charles Street West (1972, 51 floors)

8 146m 2 Bloor West (1972, 34 floors)

9 145.1m Commerce Court North (1931, 34 floors)

10 139.9m Simpson Tower (1968, 32 floors)

10 139.9m Hudson's Bay Centre (1973, 35 floors)

1981

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 239m Commerce Court West (1972, 57 floors)

4 222.9m TD Tower (1967, 56 floors)

5 183m Royal Trust Tower (1969, 46 floors)

6 180m Royal Bank Plaza South (1976, 41 floors

) 7 163m 44 Charles Street West (1972, 51 floors)

8 146m 2 Bloor West (1972, 34 floors)

8 146m Exchange Tower (1981, 36 floors)

10 145.1m Commerce Court North (1931, 34 floors)

1985

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 239m Commerce Court West (1972, 57 floors)

4 222.9m TD Tower (1967, 56 floors)

5 183m Royal Trust Tower (1969, 46 floors)

6 180m Royal Bank Plaza South (1976, 41 floors)

7 163m 44 Charles Street West (1972, 51 floors)

8 153.6m TD Waterhouse Tower (1985, 39 floors)

9 146m 2 Bloor West (1972, 34 floors)

9 146m Exchange Tower (1981, 36 floors)

1988

1 553.3m CN Tower (1976) 2 298m

First Canadian Place (1975, 72 floors)

3 274.9m Scotia Plaza (1988, 68 floors)

4 239m Commerce Court West (1972, 57 floors)

5 222.9m TD Tower (1967, 56 floors)

6 183m Royal Trust Tower (1969, 46 floors)

7 180m Royal Bank Plaza South (1976, 41 floors)

8 163m 44 Charles Street West (1972, 51 floors)

9 153.6m TD Waterhouse Tower (1985, 39 floors)

10 146m 2 Bloor West (1972, 34 floors)

10 146m Exchange Tower (1981, 36 floors)

1990

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 274.9m Scotia Plaza (1988, 68 floors)

4 263m TD Canada Trust Tower (1990, 53 floors)

5 239m Commerce Court West (1972, 57 floors)

6 222.9m TD Tower (1967, 56 floors)

7 183m Royal Trust Tower (1969, 46 floors)

8 180m Royal Bank Plaza South (1976, 41 floors)

9 163m 44 Charles Street West (1972, 51 floors)

10 153.6m TD Waterhouse Tower (1985, 39 floors)

1992

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 274.9m Scotia Plaza (1988, 68 floors)

4 263m TD Canada Trust Tower (1990, 53 floors)

5 239m Commerce Court West (1972, 57 floors)

6 222.9m TD Tower (1967, 56 floors)

7 208.1m Bay-Wellington Tower (1992, 49 floors)

8 183m Royal Trust Tower (1969, 46 floors)

9 180m Royal Bank Plaza South (1976, 41 floors)

10 163m 44 Charles Street West (1972, 51 floors)

2005

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 274.9m Scotia Plaza (1988, 68 floors)

4 263m TD Canada Trust Tower (1990, 53 floors)

5 239m Commerce Court West (1972, 57 floors)

6 222.9m TD Tower (1967, 56 floors)

7 208.1m Bay-Wellington Tower (1992, 49 floors)

8 183m Royal Trust Tower (1969, 46 floors)

9 180m Royal Bank Plaza South (1976, 41 floors)

10 176.2m One King West (2005, 51 floors)

2009

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 274.9m Scotia Plaza (1988, 68 floors)

4 263m TD Canada Trust Tower (1990, 53 floors)

5 239m Commerce Court West (1972, 57 floors)

6 222.9m TD Tower (1967, 56 floors)

7 218m Bay-Adelaide Centre West (2009, 51 floors)

8 208.1m Bay-Wellington Tower (1992, 49 floors)

[b]9 185.9m RBC Centre (2009, 42 floors)

10 183m Royal Trust Tower (1969, 46 floors)

2010

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 274.9m Scotia Plaza (1988, 68 floors)

4 263m TD Canada Trust Tower (1990, 53 floors)

5 239m Commerce Court West (1972, 57 floors)

6 222.9m TD Tower (1967, 56 floors)

7 218m Bay-Adelaide Centre West (2009, 51 floors)

8 208.1m Bay-Wellington Tower (1992, 49 floors)

9 186m Maple Leaf Square North (2010, 54 floors)

10 185.9m RBC Centre (2009, 42 floors)

2011

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 281.9m Trump International Hotel & Tower Toronto (2011, 60 floors)

4 274.9m Scotia Plaza (1988, 68 floors)

5 263m TD Canada Trust Tower (1990, 53 floors)

6 239m Commerce Court West (1972, 57 floors)

7 222.9m TD Tower (1967, 56 floors)

8 218m Bay-Adelaide Centre West (2009, 51 floors)

9 209.6m Ritz-Carlton (2011, 52 floors)

10 208.1m Bay-Wellington Tower (1992, 49 floors)

2012

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 281.9m Trump International Hotel & Tower Toronto (2011, 60 floors)

4 274.9m Scotia Plaza (1988, 68 floors)

5 263m TD Canada Trust Tower (1990, 53 floors)

6 239m Commerce Court West (1972, 57 floors)

7 222.9m TD Tower (1967, 56 floors)

8 218m Bay-Adelaide Centre West (2009, 51 floors)

9 214.5m Shangri-La Hotel & Residences (2012, 65 floors)

10 209.6m Ritz-Carlton (2011, 52 floors)

2013

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 281.9m Trump International Hotel & Tower Toronto (2011, 60 floors)

4 274.9m Scotia Plaza (1988, 68 floors)

5 263m TD Canada Trust Tower (1990, 53 floors)

6 239m Commerce Court West (1972, 57 floors)

7 238m Number One Bloor (2013, 70 floors)

8 234m Ice Condominiums East (2013, 67 floors)

9 222.9m TD Tower (1967, 56 floors)

10 218m Bay-Adelaide Centre West (2009, 51 floors)

2014

1 553.3m CN Tower (1976)

2 298m First Canadian Place (1975, 72 floors)

3 281.9m Trump International Hotel & Tower Toronto (2011, 60 floors)

4 274.9m Scotia Plaza (1988, 68 floors)

5 264m Aura at College Park (2014, 75 floors)

6 263m TD Canada Trust Tower (1990, 53 floors)

7 239m Commerce Court West (1972, 57 floors)

8 238m Number One Bloor (2013, 70 floors)

9 234m Ice Condominiums East (2013, 67 floors)

10 222.9m TD Tower (1967, 56 floors)

What an amazing change.