There was the United Provinces of New Grenada, in what is today Colombia. In 1811, they declared their independence from Spain, defeated royalist forces, and formed a parliamentary system ruled over by a triumvirate.
In 1816, the Spanish swooped in again and crushed them. That didn't last however, when Simon Bolivar's army rolled into town and freed them from Spanish rule again.
There was also the Spanish reconquest of Santo Domingo, but that wasn't a reconquest of a free colony, that was a reconquest of a colony that had fallen into the hands of the French.
I am far less familiar with it than matters regarding Cuba, but Spain reconquered the Dominican Republic in the 1860s, while the US was in the midst of the Civil War. It lost the colony again the the middle of the decade and by the time Cuba's first independence war began, in 1868, the DR was independent again.
Interestingly, Cuba's greatest general on the separatist side, Máximo Gómez, was himself Dominican.
During the classic "cycle" of Hispanic American independence (1808-1830) Cuba was basically Spain's American base of operations. The last Spanish expedition against the mainland during this period, in 1829, five thousand men sent against Mexico, also left from Cuba.
These attempts waned as Spain was heavily indebted, the expeditions kept failing, and by the early 1830s the health of the hard headed absolutist king, Fernando VII, was failing. He died in 1833 and the following years were spent in internal conflicts, with the first Carlist war (basically, absolutists and defenders of the old regime backed Carlos, brother of Fernando, and the liberals rallied around Fernando's daughter wife, Maria Cristina). [Small gaffe: Maria Cristina was Queen Regent during the childhood of Isabela II, who WAS Fernando VII's daughter]
Similar to the case of New Granada already explained, the Captaincy General of Venezuela was reconquered 2 times by the Spanish forces. The first Republic, established on July 5th 1811, was fragile as the government couldn't properly exert it's control over the confederacy, furthermore the provinces of Maracaibo, Coro and Guayana did not adhere to the independence movement and remained loyal to the crown, and in general the population as well was split between supporting or being against independence, so the Venezuelan war of independence was more of a civil war between the royalist and patriot factions than a war against Spain.
In the midst of the civil war and worsening economic situation, a key event which greatly contributed to the downfall of the republic was an earthquake which hit Venezuela on March 26 1812 which devastated the capital of Caracas among other cities. The earthquake was seen by many as God's punishment for rebelling against the crown and caused further instability in the confederacy and increased its unpopularity. Captain Domingo Monte led the royalist forces in 1812 taking advantage of the situation and inflicted serious defeats on the republicans until resistance broke down and the capitulation of San Mateo was signed, reconstituting the captaincy
However this situation would be reversed once again when a notable independence leader, Simon Bolivar, launched a counter attack in 1813 from New Granada to the west in what is known as the Admirable Campaign, which successfully led to the constitution of the second republic.
This second attempt was also short lived due to its unpopularity and especially its lack of centralization, because another military offensive, called the eastern campaign, occurred parallel to Bolivar's Admirable Campaign, led by Santiago Mariño. Mariño and Bolivar could not accept being subordinates to one another, and as such the second republic was in practice pretty much two different states.
In the llanos region of Venezuela then a caudillo (warlord) rose against the newly constituted republic: José Tomás Boves, who amassed a large army of llaneros and became very popular by promising the end of slavery for those who joined his ranks.
After several military defeats and losing Caracas to Boves' army the resistance retreated east, but is chased and finally defeated by the royalist forces. However at the battle of Urica on December 1814 Boves dies (while still being a royalist victory) which was a setback for the royalist leadership and helped strengthen Jóse Antonio Páez, another caudillo from the llanos on the republican side, who commanded many llaneros formerly under Boves.
Francisco Tomás Morales then assumed the leadership of the royalists and defeated the united provinces of New Granada in 1816 while various offensives and rebellions were carried out by disorganized independence leaders in Venezuela until the province of Guayana was liberated by Manuel Piar in 1817, becoming the nucleus of the new third republic, which would then take the fight to the Fallen New Granada, liberating it and declaring the Republic of Colombia in late 1819 (formerly constituted in 1821) as a union between New Granada and Venezuela (and later Quito and Panama).
After the decisive battle of Carabobo in 1821 the Spanish holdings wouldn’t last long, and Puerto Cabello fell in 1823 as the last royalist bastion in Venezuela. The Spanish would try to reconquer their lost colonies one last time sending another military force, which was defeated in the naval battle of Lake Maracaibo in mid-1823. Had the Spanish succeeded in this offensive they might have been able opened up a new front of operations against the republican forces.