Glasgow Rangers first visited the Oval in 1902 over the Easter period. After losing heavily to Rangers on the Easter Monday a "Glentoran United" team of seven glenmen and four other top local players defeated Rangers before a crowd of 3,000.

Rangers returned to Belfast in 1904 again over the Easter period in a game which was described as a "scrambling game". The game ended in a another win for Rangers.There would not be another fixture between
the two until in 1966.

Glentoran had only four years of european experience and now they would have to face Rangers in the first round of the European Cup Winners Cup.
The critics were expecting an comprehensive victory both home and away for Rangers but it turned out rather differently.

The first leg at the Oval seen 35,000 pack into the Oval and the Glens produced another famous display. It looked as if despite all their hard work in a battling display they would have to settle for a 0-1 loss against their more illustrious opponents but up popped Sinclair to blast home in the 89th minute. The return leg in Glasgow with a
combination of mistakes and missed chances meant that Rangers were able to run out 4-0 winners. John Colrain's shackling tactics had provided for a famous result in Belfast at the Oval. This result would lay the foundation for further success both at home and abroad.

In 2000 the Glens played Rangers again in a match that was part of Tommy Leeman's transfer 16 years previous. 2000 Glentoran supporters made the trip and in a crowd of 16,000 sang their hearts out as their team battled against a full strength Rangers team. Michael Mols scored the 1st in the 10th minute with a neat turn and shot but only Rod Wallace and Allan Johnston would score again as the part timers restricted a full strength Rangers team to a 3-0 victory.