That depends on one’s definition of the conflict that led to the Roman conquest of Bulgaria. From the initial breach of the treaty between Bulgaria and the Romans (from 927) by the Roman emperor Nikēphoros II Phōkas in 967 until the submission of Presian II of Bulgaria to the Roman emperor Basileios II in 1018 is a period of some 51 years. Thus, it was a lengthy process, with alternating periods of intensive military action and apparent inaction. The more sustained Roman invasion of Bulgaria, however, began in 971 under Iōannēs I Tzimiskēs, and resulted in the partial conquest of the country later that year. Basileios II’s campaigns against Bulgaria began in 986, and even they were permeated by gaps in the action, or at least in the evidence. In much more detail, but still a summary:
Arguably, the conflict began in 967 (Stokes thinks 966), when, flushed with success over his conquest of Cilicia and campaign in Syria, the Roman emperor Nikēphoros II Phōkas (r. 963–969) insulted the Bulgarian envoys and refused to send the customary tribute to the Bulgarian court, following this up with a show of force in Thrace. Leōn the Deacon reports that this probed across the Bulgarian border, approaching the “great fence” of Thrace — a Bulgarian earthwork stretching in an arc from Kōnstantia (by modern Simeonovgrad) to Debelt — before the emperor decided that it would be unwise to expose the Roman forces to Bulgarian ambushes; Anthony Kaldellis considers Nikēphoros’ campaign and its rationale largely fictitious. Iōannēs Skylitzēs connects the campaign with the Bulgarian failure and refusal to keep Magyar raiders from reaching Roman territory — the Bulgarian emperor Petăr I (r. 927–969) complained that the Romans had not assisted the Bulgarians against the Magyars and that, defeated by the Magyars, the Bulgarians were not going to break their recent treaty with them. At any rate, Nikēphoros had broken the 40-year peace with Bulgaria and sent a certain Kalokyros to entice the Rus’ to attack Bulgaria from the north. The Rus’ king Svjatoslav I Igorevič (r. 945–972) responded enthusiastically, invaded Bulgarian territory, defeated the Bulgarians, and returned home laden with plunder. Perhaps worried at Svjatoslav’s success, Nikēphoros subsequently patched up relations with Bulgaria and arranged for two Bulgarian princesses to marry his wards, the young Roman emperors Basileios II and Kōnstantinos VIII; Bishop Liudprand of Cremona, an envoy of the western emperor Otto I (r. 936–973), was furious at the preferential treatment given the Bulgarian envoys at the time.
Nikēphoros II Phōkas, “the Pale Death of the Saracens”:
The Rus’, however, were tempted by more plunder and expansion, Svjatoslav desiring to take up residence in the Bulgarian city of Preslavec near the Mouths of the Danube (now Nufăru in România), and Kalokyros hoping to seize the Roman throne with Rus’ assistance. Svjatoslav invaded Bulgaria again in summer 968 and proceeded to conquer 30 cities along the Danube; the Bulgarian emperor Petăr suffered a stroke, took monastic vows and died in January 969. The new Bulgarian emperor Boris II (r. 969–977) briefly diverted Svjatoslav’s attentions back to Kiev by inciting the Pečenegs to attack it, but Svjatoslav relieved his capital and returned to Bulgaria in full force. Boris capitulated, becoming effectively Svjatoslav’s protégé, as the Rus’ subjugated eastern Bulgaria and began to threaten Roman Thrace. Nikēphoros was distracted by Roman successes in the east, where Antioch was finally recovered in October 969. In December, Nikēphoros was murdered in his bedchamber, and his nephew Iōannēs I Tzimiskēs (r. 969–976) seized the Roman throne. It was Iōannēs who tackled the Rus’ invasion of the Balkans. A Rus’ force raiding into Thrace was defeated by the new emperor’s brother-in-law Basileios Sklēros at Arkadioupolis in 970, and in the spring of 971 the Romans counterattacked by land and sea, blocking the Mouths of the Danube and crossing the passes in the Balkan chain unhindered (perhaps a result of Rus’ takeover of the war effort). The emperor defeated a Rus’ force in the field, then besieged and took the Bulgarian capital Preslav by storm. Boris II now fell into his hands, receiving encouraging treatment and becoming a Roman protégé. Svjatoslav failed to counter the Roman advance before it reached his main base at Dorystolon (now Silistra), and was defeated and besieged in the city. After a few more fights, Svjatoslav was induced to treat for terms, pledging to leave and promising to never attack Romans again. During his retreat, he was ambushed and killed by the Pečenegs on the Dnieper early in 972.
The meeting between Iōannēs I and Svjatoslav I as imagined in the Madrid Skylitzēs:
The defeat of the Rus’ left the Roman emperor Iōannēs I in control of eastern Bulgaria and even some of its holdings north of the Danube. He might have initially intended to keep Boris II as a dependent ruler, but now decided to restore Roman control over long-lost lands by annexing Bulgaria. Accordingly, Iōannēs returned to Constantinople in triumph, dedicating his choicest plunder of Bulgarian imperial regalia to God and publicly stripping Boris from the signs of imperial authority, “compensating” him with appointment as magistros. As far as the Romans were concerned, Bulgaria had been conquered, and affairs in the east took priority for the rest of Iōannēs’ reign. However, the Roman conquest of Bulgaria was both temporary (largely undone in 986) and partial, since it did not comprise most of western Bulgaria. We know little of any Roman attempt to subdue that area, although we learn from a much later source that the župan of Raška (then a Bulgarian province) had fled for safety into neighboring Serbia. The Bulgarian count Nikola or his sons, the Komētopouloi (“Count’s Sons”) of the Greek sources, appear to have maintained an independent Bulgarian regime in the west, apparently in the name of the captive Bulgarian emperor Boris II, sheltering the fleeing Bulgarian patriarch and sending envoys to Otto I of Germany in 973. Following the death of Iōannēs in 976, Boris II and his brother Roman escaped — or were allowed to escape — from Constantinople and traveled west to join the “rebellion” of the Komētopouloi. Mistaken for a Roman agent on account of his clothes, Boris II was murdered by a Bulgarian border guard. Roman managed to reveal his identity on time to avoid the same fate and, although he had been made a eunuch at Constantinople, was now declared Bulgarian emperor (r. 977–997). Effective authority seems to have remained with the surviving Komētopouloi, Samuil and Aaron.
Bulgaria in c. 1000, before further losses to Romans and Hungarians:
When the new senior emperor Basilios II (r. 976–1025, though he had been junior co-emperor since 960) finally turned his attention to Bulgaria and tried to conquer Serdica (Sofia) in summer 986, he failed in his attempt to reduce the city and, after besieging it for 20 days, he began a retreat, ostensibly because of suspicions regarding the loyalty of Leōn Melissēnos in Thrace. In the Trajan’s Gate pass, Basileios II and his troops fell into a Bulgarian ambush set up by Roman, Samuil, and Aaron (16 August 986), and suffered an embarrassing defeat, barely escaping to Philippoupolis (Plovdiv). Samuil proceeded to recover control of northeastern Bulgaria, conquered parts of Thessaly, including Larissa, and eliminated internal opposition by executing his brother Aaron for being a Roman sympathizer (987). Basileios II, on the other hand, had to contend with the rebellions of the leading aristocrats and commanders Bardas Sklēros and Bardas Phōkas in 988–989, and sought the additional support of Rus’ mercenaries, offering his sister Anna as bride to the Rus’ king Vladimir I Svjatoslavič (r. 978/980–1015). The events of 986 had rekindled the war between the Roman Empire and Bulgaria, but Skylitzēs’ characterization of this as ongoing, year-by-year warfare is misleading. After defeating the rebels in 989, Basilios II did turn his attention to Bulgaria again, and campaigned there with some success in 989, 991, 992, 993, 994, before being distracted by affairs in the east. The year 991 apparently brought a significant symbolic prize, the capture of the Bulgarian emperor Roman at Skopje (Skylitzēs would seem to date this to 1003, but this inference is probably erroneous). However, Samuil continued to manage Bulgarian affairs as before, proclaiming himself Bulgarian emperor on Roman’s death in captivity in 997. In 996, the Roman general Nikēphoros Ouranos surprised and defeated Samuil and his son Gavril Radomir at the Sperkheios River on their way home from a raid deep into Greece. Although Samuil made recourse to suing for peace, he did not surrender, and some of the Roman gains were clearly fleeting. The Roman generals Theodōrokanos and Nikēphoros Xiphias succeeded in taking over northeastern Bulgaria in 1001, and the Romans seem to have retained it. Basileios II himself took Vidin in 1002, just before Samuil plundered the fair at Adrianople in 1003.
Samuil at the wedding of his daughter Miroslava, from the Madrid Skylitzēs:
For the next decade, Skylitzēs’ account is silent, apart from the formulaic statement that Basileios II continued to attack Bulgaria every year. The effective absence of any indications has led to the suggestion that Basileios II and Samuil may have made peace. That, or possible Bulgarian recovery, might have been worth obscuring in later narratives. When Skylitzēs’ information on the Bulgaro-Roman war resumes in 1014, Samuil was holding the Kleidion Pass against Basileios II, until the latter’s general Nikēphoros Xiphias succeeded in finding his way around the Bulgarian positions from the opposite direction. Samuil escaped but most of his army was captured and — according to tradition — blinded. Samuil is said to have suffered a heart attack and died two days later, on 6 October 1014. Nevertheless, Bulgaria fought on, under the seemingly less able leadership of Samuil’s son Gavril Radomir (r. 1014–1015), even as Basileios II was able to take or raze additional Bulgarian strongholds. Gavril Radomir was murdered and succeeded by his cousin, Aaron’s son Ivan Vladislav (r. 1015–1018), whose life he had saved decades earlier. Like Gavril Radomir before him, Ivan Vladislav made overtures for peace to Basileios II, while continuing to resist. Basileios II pressed on, burning the Bulgarian palaces at Bitola and capturing Ohrid, before one of his forces was destroyed by the Bulgarian commander Ivac and the Roman emperor returned home to Constantinople in January 1016. Returning to the field later the same year, Basileios II faced determined opposition — he failed to take Pernik, then (1017) Kastoria, although he defeated an ambush by Ivan Vladislav and a threatened Bulgaro-Pečeneg alliance on the Lower Danube failed to materialize.
Basileios II returned to Constantinople in January 1018, with no end in sight for the war. A month later, he learned that Ivan Vladislav had been killed in battle before the walls of Dyrrakhion (Durazzo). Curiously, despite the turnover on the Bulgarian throne and the plethora of Roman successes — admittedly, reported by Roman sources — in previous years, it was only now that Bulgarian resistance really crumbled. Even as Basileios II was approaching Bulgaria, he received the submission of numerous Bulgarian nobles and commanders, individually or in groups. The three eldest sons of Ivan Vladislav, led by Presian II (r. 1018), attempted to continue resistance from the Tomor Mountain (in Albania today), but eventually (August 1018) they joined their mother and siblings, who had already surrendered to Basileios. He could afford to be generous with various awards and high court dignities meted out to his new subjects. Like Boris II and Roman before him, Presian II became a magistros; his brothers became patrikioi; their mother Marija received the highest female dignity at court, zōstē patrikia. Basileios II’s final annexation of Bulgaria in 1018 was more an imperial tour than a military conquest; it ended in a triumph celebrated at Athens — he was the first emperor to show up there since Kōnstas II (r. 642–668) in the 660s. It is not to say there was no more strife: Kōnstantinos Diogenēs eliminated the local Bulgarian governor and took over Sirmium in 1019. At any rate, the Roman conquest of Bulgaria could finally be described as complete in the late summer of 1018. Partly interrupted by major revolts in 1040–1041 and 1072, Roman rule over Bulgaria would last until 1186.
The triumph of Basileios II over Bulgarians and Armenians:

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